CA2323003A1 - Novel cationic 2-acylaminophenols, their use as coupler for oxidation dyeing, compositions containing them, and dyeing methods - Google Patents

Abstract

The invention concerns novel cationic 2-acylaminophenols of formula (I) comprising at least a cationic group, their use as coupler for oxidation dyeing of keratin fibres and in particular human keratin fibres such as hair, oxidation dyeing compositions containing them combined with at least an oxidation base, and oxidation dyeing methods using them.

Description

NOVEL CATIONIC 2-ACYLAMINOPHENOLS, THEIR USE
AS A COUPLER FOR OXIDATION DYEING, COMPOSITIONS COMPRISING THE SAME, AND DYEING METHODS
The subject of the invention is new cationic 2-acylaminophenols of formula (I) comprising at least one cationic group, their use in title of coupler for the oxidation dyeing of keratin fibers and in particular human keratin fibers such as the hair, the compositions of oxidation dye containing them in association with at least one base oxidation, and the oxidation dyeing processes using them.
It is known to dye keratin fibers and in particular the hair humans with dye compositions containing precursors of oxidation dye, in particular ortho or paraphenylenediamines, ortho or paraaminophenols, heterocyclic compounds such as diaminopyrazole derivatives, generally called oxidation bases. The oxidation dye precursors, or oxidation bases, are compounds colorless or faintly colored which, associated with oxidizing products, can give birth by a process of oxidative condensation to colored and coloring compounds.
We also know that fon can vary the nuances obtained with these oxidation bases by associating them with couplers or modifiers of coloring, the latter being chosen in particular from metadiamines aromatics, metaaminophenols, metadiphenols and certain compounds heterocyclic.
The variety of molecules involved in the oxidation bases and couplers, allows obtaining a rich palette of colors.
SUBSTITUTE SHEET (RULE 26)

2 The so-called "permanent" coloration obtained thanks to these oxidation dyes, must moreover satisfy a certain number of requirements. So she must be without toxicological disadvantage, it must make it possible to obtain shades in the desired intensity and present good resistance to agents exteriors (light, bad weather, washing, permanent ripple, perspiration, friction).
The dyes should also cover white hair, and finally be the least selective possible, that is to say allow to obtain deviations of weakest tones possible throughout the same fiber keratin, which can indeed be sensitized differently (ie damaged) between its tip and its root.
To obtain red shades, we generally use, alone or in mixture IS with other bases, and in combination with appropriate couplers, 4-aminophenol, and to get blue shades, we usually do use of para-phenylenedtamines. The use of couplers derived from metaphenylenediamines, in combination with derivatives of paraphenytenediamines, usually leads to blue shades of generally poor strength.
It has already been proposed, in particular in patent FR-A-1,596,879, to use for oxidation tincture of keratin fibers, phenolic derivatives substituted in position 2 by a ureinyl or thioureinyl radical, in association with para-phenylenediamine derivatives, in order to obtain nuances close to those obtained with couplers derived from metaphenylenediamines. However, the dye compositions containing the compounds cited in this patent generally lead to hair on colors too selective and lacking in intensity.
SUBSTITUTE SHEET (RULE 26)

3 Furthermore, it has already been proposed, in particular in patent BE 816 674, to use for dyeing keratin fibers, in combination with derivatives of para-phenylenediamines, phenolic derivatives substituted in position 2 by an acetyl or ureic radical and in position 5 by a halogen atom, to to obtain dyes ranging from green to blue-green. Tenacities to the light of shades obtained on hair by using these compositions are generally better than those obtained with compositions dyes containing one or more metaphenylenediamines as couplers. However, weathering and washing toughness, as well as the intensities of the colorings obtained are still too low and constitute in these points major drawbacks for those skilled in the art.
In addition, it has already been proposed, in particular in the patent application.
EP 0 579 204, to use, for dyeing keratin fibers, derivatives IS non cationic phenol substituted in position 2 by a radical acylamino, carbamoyl or ureyls, and in position 5 by a C 1 -C 4 alkyl radical, in combination with paraphenylenediamine derivatives. However, the use phenolic derivatives cited in this European patent application do not not allow to obtain a rich palette of colors, and moreover the nuances blue generally obtained are not entirely satisfactory in this which concerns their resistance to washing and the action of light.
The plaintiff has now just discovered, in a totally unexpected and surprising, that new 2-acylaminophenols of formula (I) defined below comprising at least one cationic group of formula (II) defined below, not only suitable for use as coupler, but also that they make it possible to obtain compositions dye leading to powerful colors, in a wide palette of colors, and with excellent resistance properties to different treatments than can undergo keratin fibers.
SUBSTITUTE SHEET (RULE 26)

4 These discoveries are the basis of the present invention.
The first object of the invention is therefore new 2-acylaminophenols cationic compounds of formula (I) and their addition salts with an acid CWI ~~ BI ~ k ~ A ~ I ~ B2 ~~ W2 ~ (I) in which - the group A represents a group represented by the group D
as defined below;
- B, and Bz, independently of each other, represent a group represented by group B as defined below;
- k, I and m are whole numbers, which can independently take the from each other, the value 0 or '1; the sum k + I + m being different from zero;
- W, and W2 represent, independently of one another, a group W
represented by the following formula (II) .OH R ~
R5 ~ N s O
6 ~ Z
R4. _ Ra Y
formula (II) in which ~ R, represents a hydrogen atom; a group Z as defined below; a radical containing from 1 to 15 carbon atoms, linear or SUBSTITUTE SHEET (RULE 26}

WO 00/43368 PCT / F'R00 / 00143 branched (the branch or branches can form one or more cycles carbonaceous with 3 to 7 links), which may contain one or more double bonds and / or uné or several triple bonds (the said bonds double possibly leading to aromatic groups), of which

5 one or more carbon atoms can be replaced by an atom oxygen, nitrogen, or sulfur or by an S02 group, and whose carbon atoms can, independently of each other, be substituted by one or more halogen atoms; it being understood that said group S02 is not directly connected to the nitrogen atom in position 7 bearing the radical R,; said radical R, not comprising a peroxide bond nor diazo, vitro or nitroso radicals; it being understood that the radical R,; born does not represent a hydroxy, amino, thio, alkoxy and alkylthio radical.
~ R2 represents a hydrogen atom; a group Z as defined below; a radical containing from 1 to 20 carbon atoms, linear or branched (the branch or branches can form one or more carbon rings with 3 to 7 links), which can contain one or more links double and / or one or more triple bonds (said double bonds possibly leading to aromatic groups), and one or several carbon atoms can be replaced by one atom oxygen, nitrogen, or dè. sulfur or by an S02 group, and whose carbon atoms can, independently of each other, be substituted by one or more halogen atoms; said radical R2 does comprising no peroxide bond nor diazo, vitro or nitroso radicals; and it being understood that RZ cannot represent a hydroxyl or thio radical;
~ the radicals R, and R2 can, in addition, be linked to form a cycle saturated or unsaturated comprising from 5 to 7 links, consisting of carbon, of nitrogen, oxygen, sulfur and / or by group C = O, each link being substituted or unsubstituted by 1 or 2 radicals R, identical or different, R
being a linear or branched C, -Cs alkyl radical (the branch or branches SUBSTITUTE SHEET (RULE 26)

6 can then form one or more rings with 3 to 6 links), may contain one or more double bonds and / or one or more triple bonds (said double bonds possibly leading to aromatic groups), and of which one or more carbon atoms may be replaced by an oxygen, nitrogen, or sulfur atom or by an S02 group, and whose carbon atoms can, independently of each other, be substituted by one or more halogen atoms; said radical R not comprising a peroxide bond nor diazo, nitro or nitroso radicals;
~ R3, R4 and R5, identical or different, represent a hydrogen atom or halogen; a group Z as defined below; a radical comprising from 1 to 20 carbon atoms, linear or branched (the branch (es) can then form one or more rings with 3 to 7 links), may contain one or more double bonds and / or one or more triple bonds (said double bonds possibly leading to aromatic groups), and of which one or more carbon atoms can be replaced by an oxygen, nitrogen, or sulfur atom or by an S02 group, and whose carbon atoms can, regardless. each other, be substituted by one or more halogen atoms; said radicals R3, R4 and R5 not comprising bonding peroxides or diazo, vitro or nitroso radicals; and it being understood that R5 cannot represent a hydroxyl, thio or amino radical or a group substituted or unsubstituted sulfonylamino; and it being understood that the radicals R3, R4 and R5 cannot be linked to the benzene ring of formula (II) by a -NH-NH- bond;
the radicals R, and R3 can also be linked to form a saturated cycle comprising from 6 to 7 links, consisting of carbon, nitrogen, oxygen, sulfur and / or by group C = O, each link being substituted or not substituted by 1 or 2 radicals R, identical or different, R having the same SUBSTITUTE SHEET (RULE 26)

7 meanings as those indicated above; said radical R does comprising no peroxide bond nor diazo, nitro or nitroso radicals;
R2 and R3 can also be linked to form a ring saturated comprising of ~ ~ with 7 links, consisting of carbon, nitrogen, of oxygen, sulfur and / or by group C = O, each link being substituted or unsubstituted by 1 or 2 radicals R, identical or different, R having the same meanings as those indicated above; said radical R does comprising no peroxide bond nor diazo, nüro or nitroso radicals;
~ Y represents a hydrogen or halogen atom; a group -ORs, -SRs or -NH-S02Rs in which Rs represents a C 1 -C 6 alkyl radical, linear or branched (the ramifications can then form one or several cycles with 3 to 6 links), substituted or unsubstituted by one or more radicals chosen from the group consisting of an atom halogen, hydroxy, C, -C4 alkoxy, amino and aminoalkyl C, -C4; a phenyl radical substituted or unsubstituted by one or two radicals selected from the group consisting of a C 1 -C 4 alkyl radical trifluoromethyl, carboxy, C, -C4 alkoxycarbonyl, halogen, hydroxy, C 1-4 alkoxy, amino, and C 1-4 aminoalkyl; or a benzyl radical; and it being understood that Y cannot represent -NH-S02R6 when R3 represents a hydroxy radical;
~ Z is a cationic group represented by the following formula (IV) (B) n ~ (IV) in which - B represents a radical comprising from 1 to 15 carbon atoms, linear or branched (the branch or branches can then form one or more rings with 3 to 7 links), which may contain one or more SUBSTITUTE SHEET (RULE 26) WO 00/4336

8 PCT / FR00 / 00143 double bonds and / or one or more triple bonds, said bonds double possibly leading to aromatic groups, and one or more carbon atoms of which may be replaced by one oxygen, azd'te, or sulfur atom or by an SO2 radical; and one of which or several carbon atoms can, independently of the ones of others, be substituted by one or more halogen atoms or by one or several Z groups; said radical B not comprising a bond peroxide or radicals.diazo, nitro or nitroso;
i0 - D is chosen from cationic groups of formulas (V) and (VI) following N Rs / _ X- R N + X-Z '' (V) (VI) in which - the radical B is linked to the group D by any one of the atoms of the radical D;
- n and p pewent, independently of each other, take the value 0 or 1;
- when n = 0, then the group of formula (VI) can be linked to compound of formula (II) directly by the nitrogen atom of ammonium quaternary, in place of the radical R, o.
SHEET. REPLACEMENT (RULE 26)

9 - Z ,, Z2, Z3, and Z4, independently of each other, represent a oxygen atom; a sulfur atom; a substituted nitrogen atom or unsubstituted by a radical R "; or a substituted carbon atom or unsubstituted by one or two radicals R ", identical or different;
- Z5 represents a nitrogen atom; or a substituted carbon atom or unsubstituted by a radical R ";
- Z6 can have the same meanings as those indicated below for the radical R ", it being understood that Zs is different from an atom hydrogen;
the radicals Z, or ZS can, moreover, form with Ze a saturated cycle or unsaturated comprising from 5 to 7 links, each link being substituted or unsubstituted by one or two identical or different R "radicals;
- R "represents a hydrogen atom; a group Z; a radical containing from 1 to 10 carbon atoms, linear or branched, capable of contain one or more double bonds and / or one or more bonds triple, said double bonds then possibly leading to aromatic groups, and one or more carbon atoms of which can be replaced by an oxygen, nitrogen, or sulfur atom, or by a group SO2, and of which one or more carbon atoms may, independently of one another, be substituted by one or several halogen atoms; said radical not comprising a bond peroxide or diazo, nitro or nitroso radicals;
two of the adjacent radicals Z ,, Z2, Z3, Z4 and Z5 can also form a cycle comprising from 5 to 7 links, each link being independently represented by a substituted or unsubstituted carbon atom substituted by one or two identical or different R "radicals; an atom SUBSTITUTE SHEET (RULE 26) WO 00/43368 PCT / F1t00 / 00143 of nitrogen substituted or unsubstituted by a radical R "; an atom oxygen; or a sulfur atom;
- R ,, Re, Rs, and R, o, identical or different, have the same sign ~ cations 5 than those indicated above for the radical R ";
the radicals R ,, Ra and R9 can also form, two by two with (quaternary nitrogen atom to which they are attached, one or more saturated cycles comprising from 5 to 7 links, each chain not being independently represented by a substituted or unsubstituted carbon atom

10 substituted by one or two identical or different R "radicals; an atom of nitrogen substituted or unsubstituted by a radical R "; an atom oxygen; or a sulfur atom;
- X 'represents an organic or mineral anion and is preferably chosen in the group consisting of a halide group such as chloride, bromide, fluoride, iodide; a hydroxide; a sulfate; a hydrogen sulfate; a (C, -Ce) alkyl sulfate such as for example a me # hylsulfate or an ethylsulfate; an acetate; a tartrate; an oxalate; a (C, -C6) alkyl sulfonate such as methylsulfonate; a substituted arylsulfonate or unsubstituted by a C 1 -C 4 alkyl radical such as for example a 4-toluylsulfonate;
Being heard that - the radical B, is linked to the group A by any one of the atoms of radical A;
- when k = 0, then the group A can be linked to the group W, directly by (nitrogen atom of the quaternary ammonium, instead of radical R, o;
- the radical B2 is linked to the group A by any one of the atoms of radical A;
REPLACEMENT SHEET (RULE 2fi)

11 - when m = 0, then group A of formula (VI) can be linked to group W2 directly by the nitrogen atom of (quaternary ammonium, to the place of the radical R, o.
the group B, of formula (I) is linked to an atom of the group W, and that this atom is identified by an asterisk (*) on the skeleton of W, represented by formula (III) defined below;
- the group B2 is linked to an atom of the group W2 and that this atom is identified by an asterisk (*) on the skeleton of W2 represented by the formula (III) defined below;
OH
N ~ O
* 18 Y
(III) - when k + I = 0, then W, and / or W2 and / or B2 contain at least one group Z
- when I + m = 0, then W, and / or W2 and / or B, contain at least one group Z
- when I = 1, then k and m, independently fun of the other, can take the values 0 and 1.
As previously stated, the oxidation dye composition containing the compound or compounds of formula (I) in accordance with (invention allows obtain powerful colors in shades ranging from red to blue and also showing remarkable tenacity in the various treatments that can undergo keratin fibers. These properties are particularly remarkable especially with regard to the resistance of colorings obtained with regard to the action of light, bad weather, washing, permanent waving and sweating.
SUBSTITUTE SHEET (RULE 2ô)

12 According to the invention, and when it is indicated that one or more of the atoms of carbon of the radical (s) R, to R5, can be replaced by an atom oxygen, nitrogen, or sulfur or by an S02 group, and / or that said radicals R, to RS which may contain one or more double bonds and / or a or more triple bonds, this means that fon can, for example, make the following transformations -CHi HP ~ hold; - ~ -H
can become 'can become ~ - ~ S ~ NI ~
can become According to the invention, R, preferably denotes a hydrogen atom, a radical Z; a group A ,, A2, A3, A4 or As, optionally separated from the nitrogen located in position 7 on which the radical R is fixed, by a group - (COr.
According to the invention, the term “group A” is intended to mean a C 1 -C 6 alkyl radical, linear or branched, can carry one or two double bonds or a triple bond, be substituted or unsubstituted by a group chosen from a group A2, group A4, and group A5, whether or not substituted substituted by one or two groups, identical or different, chosen from N-alkyl (C, -C3) amino groups, N-alkyl (C, -C3 ~ N-alkyl (C, -C3) amino, alkoxy (C, -Cs), oxo, alkoxycarbonyl, acyioxy, amide, acylamino, ureyl, sulfoxy, sulfonyl, sulfonamido, sulfonylamino, bromo, cyano, carboxy, and be substituted or unsubstituted by one or more hydroxyl, fluoro or chloro groups.
SUBSTITUTE SHEET (RULE 26)

13 By group A2 is meant an aromatic group of phenyl type or naphthyl, which may be substituted or unsubstituted by one to three groups, identical or different, chosen from methyl groups, trifluoromethyl, ethyl, isopropyl, butyl, pentyl, fluoro, chloro, bromo, methoxy, trifluoromethoxy, ethoxy, propyloxy, acetyloxy, acetyl, and cyano.
By group A3 is meant a heteroaromatic group chosen from ies furanyl, thiophenyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyle, 1,2; 3-triazolyle, 1,2,4-triazolyle, isoxazolyle, isothiazolyle, pyrazolyle, pyrazoltriazolyle, pyrazoloimidazolyle, pyrrolotriazolyle, pyrazolopyrimidyle, pyrazolopyridyle, pyridyle, pyrimidyle, benzoimidazolyle, benzoxazolyle, benzothiazofyle, indolyle, indolidinyle, isoindolyle, indazolyle, benzotriazolyl, quinolinyl, benzoimidazolyle, benzopyrimidyle, said groups being substituted or unsubstituted by 1 to 3 radicals chosen from the radicals C, -C ,, linear or branched alkyl, C, -C ,, monohydroxyalkyl CZ-C4 polyhydroxyalkyl, carboxy, alkoxycarbonyl, halogen, amido, amino and hydroxy.
The term “A4 group” is intended to mean a C3-C cycloalkyl radical, a radical norbomanyl, with or without a double bond and substituted or unsubstituted with 1 or 2 radicals chosen from C 1 -C 4 alkyl radicals, linear or branched, monohydroxyalkyle in C, -C4, polyhydroxyalkyle in C2-C4, carboxy, alkoxycarbonyl, halogen, amido, amino and hydroxy.
By group A5 is meant a heterocycle chosen from the cycles by dihydrofuranyl, tetrahydrofuranyl, butyrolact-one-yl, dihydrothiophenyl, tetrahydrothiophenyl, tetrahydrothiophen-one-yl, iminothiolane, dihydropyrrolyle, pyrrofidinyle, pyrrolidin-one-yle, imidazolidin-one-yle, imidazolidinthione-yle, oxazolidinyl, oxazolidin-one-yle, oxazolanethione, thiazolidinyl, isothiazol-one-yl, mercaptothiazolinyl, pyrazolidin-one-yl, iminothiolane, dioxolanyl, pentalactone, dioxanyie, dihydropyridinyle, SUBSTITUTE SHEET (RULE 26) WO 00/43368 PG "f / P'R00 / OOL43

14 piperidinyl, pentalactam, morpholinyl, pyrazoli (di) nyle, pyrimi (di) nyl, pyrazinyl, piperazinyl and azepinyl.
Among these substituents, R, preferably represents a hydrogen atom; a methyl, ethyl, isopropyl, allyl, phenyl, benzyl, fluorobenzyl radical, hydroxybenzyle, difluorobenzyle, trifluorobenzyle, chlorobenzyle, bromobenzyl, methoxybenzyl, dimethoxybenzyl, (trifluoromethoxy) benzyl, 3,4-methylendioxybenzyl, 6-chloropiperonyl, 4-methylthiobenzyl, 4-methylsulfonylbenzyl, 4-acetylaminobenzyl, 4-carboxybenzyl, 1-naphthomethyl, 2-naphthomethyl; or a 2-hydroxyethyl group, 2-methoxyethyl or 2-ethoxyethyl.
Even more preferably, R represents a hydrogen atom or a methyl radical.
According to the invention, R2 preferably denotes a hydrogen atom, a amino group; a group Z; a group A ,, a group A2, an A3 group, an A4 group or an AS group as defined previously, possibly separated from the carbon (in position 8) of the function amide of the compound of formula (II) by a group -O-, -NH, or -NAlkyl (C, -C3).
Among these substituents, RZ preferably denotes a group Z; a radical chosen from the group (G1) consisting of a methyl, ethyl, propyl radical, isopropyl, butyl, isobutyl, tort-butyl, pentyl, isopentyl, neopentyl, hexyl; cyclopropyie, cyclobutyle, cyclopentyie, cyctopentylméthyl, 3-cyciopentyl-propyl, cyclohexyl, 2-cyclohexyl-ethyl, norbomane-2-yl, vinyl, 1-methylvinyl, 2-methylvinyl, 2,2-dimethylvinyl, allyl, 3-butenyl ;
phenyl, methylphenyl, dimethylphenyl, 2,4,6-trimethylphenyl, 4-ethylphenyl, (trifluoromethyl) phenyl, hydroxyphenyl, methoxyphenyl, ethoxyphenyl, acetoxyphenyia, (trifluoromethoxy) phenyl, aminophenyl, SUBSTITUTE SHEET (RULE 26) 4-dimethylaminophenyl, fluorophenyl, difluorophenyl, fluoro (trifluoromethyl) phenyl, chlorophenyl, dichlorophenyl, bromophenyl, napht-1-yl, napht-2-yl, (2-methoxy) napht-1-yl, benzyl, 4'-methoxybenzyl, 2 ', 5'-dimethoxybenzyl, 3', 4'-dimethoxybenzyl, 4'-fluorobenzyl, 5 4'-chlorobenzyl, phenethyl, 2-phenylvinyl, (1-naphthyl) methyl, (2-naphthyl) methyl; tetrahydrofuran-2-yl, furan-2-yl, 5-methyl-2- (trifluoromethyl) furan-3-yl, 2-methyl-5-phenyifuran-3-yl, thiophene-2-yl, (thiophene-2-yl) methyl, 3-chlorothiophene-2-yl, 2,5-dichlorothiophene-3-yl, benzothiophene-2-yl, 3-chlorobenzothiophene-2-yl, isoxazole-5-yl, 10 5-methylisoxazole-3-yl, 3,5-dimethylisoxazole-4-yl, 1,3-dimethylpyrazole-5-yl, 1-ethyl-3-methylpyrazole-5-yl, 1-tertbutyl-3-methylpyrazole-5-yl, 3-tertbutyl-1-methylpyrazole-5-yl, 4-bromo-1-ethyl-3-methylpyrazole-5-yl, indole-3-ylcarboxyi, pyridinyl, chloropyridinyl, dichloropyridinyl, 5- (bromo) pyridin-3-yl, piperazin-2-yl, quinoxal-2-yl; fluoromethyl, difluoromethyl, trifluoromethyl,

1,1,2,2-tetrafluoroethyl, pentafluoroethyie, heptafluoropropyte, 1,1,2,2,3,3,4,4-octafluorobutyl, nonafluorobutyl, chloromethyl, chloroethyl, 1,1-dimethyl-2-chloroethyl, 1,2-dichloroethyl, 1-chloropropyl, 3-chloropropyl, 4-chlorobutyl, hydroxymethyl, methoxymethyl, phenoxymethyl, (4-chlorophenoxy) methyl, benzyloxymethyl, acetoxymethyl, 1,2-dihydroxyethyl, 1-phenoxyethyl, 1-acetoxyethyl, 2- (2-carboxyethoxy) ethyl, 1-phenoxyethyl, 1-acetoxyethyl, methoxycarbonyl, ethoxycarbonyl, (methoxycarbonyl) methyl, 2-carboxyethyl, 2- (methoxycarbonyl) ethyl, 2-carboxycylopropyl, 2-carboxycyclohexane;
methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, pentoxy, neopentoxy, hexyloxy, cyclopentyloxy, cyclohexyloxy, vinyloxy, allyloxy, propargyloxy, chloromethoxy, 1-chloroethoxy, 2-methoxyethoxy, 4-chlorobutoxy, phenoxy, 4-methyphenoxy, 4-fluorophenoxy, 4-bromophenoxy, 4-chlorophenoxy, 4-methoxyphenoxy, naphth-2-yioxy, benzyloxy; amino, methylamino, ethylamino, propylamino, isopropyiamino, butylamino, cyclohexylamino, allylamino, 2-chloroethylamino, 3-chloropropylamino, carboxymethylamino, phenylamino, fluorophenylamino, (trifluoromethyl) phenylamino, SUBSTITUTE SHEET (RULE 26) WO 00 / 433b8 PCT / FR00 / 001 ~ 3

16 chlorophenylamino, bromophenylamino, 4-acetylphenylamino, methoxyphenylamino, (trifluoromethoxy) phenylamino, naphth-1-ylamino, benzylamino, phenethylamino, pyrid-3-ylamino, dimethylamino, 1-pyrolidinyl, 4-morpholinyl.
When R, and RZ form a cycle, said cycle is preferably chosen from the 2-pyrrolidinon-1-yl, methyl-2-pyrrolidinon-1-yl, 5-carboxy- groups 2-pyrrolidinon-1-yl, 5-methoxycarbonyl-2-pyrrolidinone-1-yl, pyrazolinone-1-yl, succinimide-1-yl, 3,5-diketopyrazolidin-1-yl, oxindolin-1-yl, maleimide-1y1, isoindole-1,3-dione-2-yl, 2-piperidinone-1-yl, and glutarimide-1-yl.
Even more preferably, R2 represents a radical chosen from the group (G2) consisting of a methyl, ethyl, propyl, allyl radical, phenyl, tetrahydrofuran-2-yl, furan-2-yl, thiophene-2-yl, pyridinyl, piperazin-2-yl, fluoromethyl, chloromethyl, 2-chloroethyl, methoxymethyl, acetoxymethyl, 1,2-dihydroxyethyl, methoxycarbonyl, 2-carboxyethyl, methoxy, ethoxy, propoxy, allyloxy, 2-chloroethoxy, 2-methoxyethoxy, amino, ethylamino, allylamino, 2-chloroethylamino, pyridylamino, dimethylamino, 1-pyrolidinyl, and 4-morpholinyl; or a group -D ,, -ED ,, -OED ,, -NH-ED ,, in which -E- represents an arm - (CH2) q, q being an integer equal to 1 or 2, and D, represents a group D 'chosen from the groups 3-methylimidazolidinium-1-yl, 3- (2-hydroxyethyl} -imidazolidinium-1-yl, 1,2,4-trlazolinium-1-yl, 1,2,4-triazolinium-4-yl, N-alkyl (C, -C4) pyridinium-2-yl, N-alkyl (C, -C4) pyridinium-3-yl, N-alkyl (C, -C4) pyridinium-4-yl, N- (2-hydroxyethyl) pyridinium-2-yl, N- (2-hydroxyethyl) pyridinium-3-yl, N- (2-hydroxyethyl) pyridinium-4-yl, pyridinium-1-yl, trialkyl (C, -C4) ammonium-N-yl, 1-methylpiperidinium-1-yl and 1,4-dimetylpiperazinium-1-yl.
Even more preferably, RZ represents a methyl radical, methoxymethyl, 2-carboxyethyl, methoxy, amino, ethylamino, 1-pyrolidinyl;
SUBSTITUTE SHEET (RULE 26) WO 00 / 433b8 PCT / FR00 / 00143

17 a group -D ,, -ED ,, -OED ,, -NH-ED ,, in which -E- represents a arm - (CHZ) Q, q = 1 to 2, and D, a group D 'as defined above;
According to (invention, R3 and R4, identical or different, preferably denote a hydrogen or halogen atom; a hydroxyl or amino group; a group Z; a group A, as defined above; a group A ,, A2, A3, A ,, or A5 as defined above and separated from the nucleus phenolic of formula (II) by an oxygen atom or by a group -NH-, -Nalkyl (C, -C3) -, -NH (CO) -, -Nalkyl (C, -C3) CO) -, -NH [C = NH] -, -NH (CO) NH-, -NH (CO) Nalkyl (C, -C3 ~, -NH (CO) O-, -NHS02, -NHSOZNH-, or -NHS02Nalkyl (C, -C3) -.
Among these substituents, R3 represents even more preferably an atom hydrogen or chlorine; a group Z; a methyl radical, hydroxymethyl, methoxymethyl, 1-hydroxyethyl, aminomethyl, methylaminomethyl, hydroxy, methoxy, amino, methylamino, or 2-hydroxyethylamino; a group -NH (CO) R, 2 in which R, 2 represents one of the radicals listed in the group (G1) as defined above; a group -NHS02R, 3, in which R, 3 represents one of the radicals listed in the group (G3) consisting of the methyl, trifluoromethyl and ethyl radicals, 2-chloroethyl, propyl, 3-chloropropyl, isopropyl, butyl, thiophene-2-yl, hydroxy, ethoxy and dimethylamino.
When R, and R3 form a cycle, together with the nitrogen atom position 7 of the compound of formula (II), the bond for -R, R3 is preferred -CH2CH2CH2-.
When R2 and R3 form a ring, together with (nitrogen atom in position 7 of the compound of formula (II), the bonds - R2R3- are preferred -CH2-, -C (CH3) 2-, or -CH2CH2-.
SUBSTITUTE SHEET (RULE 26) WO 00/43368 PCT / F'R00 / 00193

18 Even more preferably, R3 represents a hydrogen atom; a methyl radical, hydroxymethyl, aminomethyl, hydroxy, methoxy, amino, methyiamino; a methanesulfonylamino group; ethanesulfonylamino;
dimethylamino-sulfonyiamino; a group -NH (CO) R, 4 in which R, 4 represents fun of the radicals listed in the group (G2) as denial above ;
or a group -OE-D2, -NH-E-D2, -NH (CO) -D2, -NH (COrE-D2, -NH (CO) OE-D2, -NH (CO) NH-E-D2, or -NH (S02 ~ E-D2, in which -E- has the same meaning as indicated above and DZ represents a group D 'as defined above.
Among these substituents, R4 preferably represents a hydrogen atom or chlorine; a group Z; a methyl, ethyl, hydroxymethyl radical, methoxymethyl, aminomethyl, methylaminomethyl, hydroxy, methoxy, acetoxy, amino, methylamino, N-piperidino, or N-morpholino; a group -NH (CO) R, 5 in which R, 5 represents fun of the radicals listed in the group (G1) defined above; or a group -NHS02R, 8 in which R, g represents fun of the radicals listed in the group (G3) defined above.
Even more preferably, R4 represents a hydrogen atom or chlorine; a methyl, hydroxymethyl, aminomethyl, hydroxy, methoxy radical, amino, or methylamino; a methanesulfonyiamino group;
ethanesulfonylamino; dimethylaminosulfonylamino; a group -NH (CO) R "in which R" represents one of the radicals listed in the group (G2) defined above; or a group -OE-D3, -NH-E-D3, -NH (CO) -D3, -NH (CO ~ E-D3, -NH (CO) OE-D3, -NH (CO) NH-E-D3, or -NH (SOZ) -E-D3, in which -E- has the same meaning as that indicated above, and D3 represents a group D 'as defined above.
According to the invention, R5 is preferably chosen from a hydrogen atom or halogen; a group Z; an A group, as defined previously; a group A ,, A2, A3, A4 or AS as defined SUBSTITUTE SHEET (RULE 26)

19 previously and separated from the phenolic nucleus of the compounds of formula (II) by an oxygen or sulfur atom, or by an -NH- group, -Nalkyl (C, -C3-NH (COJ-, -Nalkyl (C, -C3) (CO) -, -NH [C = NH] -, -NH (CO) NH-, -NH (CO) Nalkyl (C, -C3) -, ~ or -NH (CO) O-.
Among these substituents, R5 preferably represents a hydrogen atom, of chlorine, fluorine, or bromine; a group Z; a methyl radical, trifluoromethyl, allyl, methoxy, or methylamino; or a group -NH (CO) R, 8 in which R, e represents fun of the radicals listed in the group (G1) defined above.
Even more preferably, R5 represents a hydrogen atom, chlorine, or fluorine; a methyl, hydroxymethyl, aminomethyl radical, methoxy, or methylamino; a group -NH (CO) R, 9 in which R, 9 represents a radicals listed in the group (G2) defined above; or a group -OE-D4, -NH-E-D4, -NH (CO) -D4, -NH (CO) -E-D4, -NH (CO) OE-D4, -NH (CO) NH-E-D4, in which -E- has the same meaning as that indicated above, and D4 represents a group D 'tei as defined above.
According to the invention, Y is preferably chosen from a hydrogen atom, of chlorine, fluorine, or bromine; a methoxy, ethoxy, propoxy group, benzyloxy, phenoxy, -OCH2CH20CH3; -OCH2CH20CH3; -OCH2CHZN (CH3) 2;
-OCH2 (CO) OH, -OCH2 (CO) OCH3, -OCHZ (CO) OC2H5, -SCHzCH2C02H, or -NHSOZCH3; it being understood that Y cannot represent a group -NHS02CH3 when R3 represents a hydroxyl radical.
Even more preferably, Y represents a hydrogen atom or chlorine; or a methoxy group, -OCH2 (CO) OH, or -OCH2 (CO) OCH3.
Among the groups D, there may be mentioned, by way of example, the groups imidazolinium, thiazolinium, oxazolinium, pyrrolinium, 1,2,3-triazolinium, SUBSTITUTE SHEET (RULE 26) 1,2,4-triazolinium, isoxazolinium, ixothiazounium; imidazolidinium, thiazolidinium, pyrazolinium, pyrazolidinium, oxazolidinium, pyrazoltriazolinium, pyrazoloimidazolinium, pynrolotriazolinium, pyrazoiopyrimidinium, pyrazolopyridinium, pyridinium, pyrimidinium, pyrazinium, triazinium, 5 benzoimidazolinium, benzoxazolinium, benzothiazolinium, indolinium.
indoüdinium, isoindolinium, indazolinium, benzotriazolinium, quinolinium, tetrahydroquinolinium, benzoimidazofidinium, benzopyrimidinium, tetra-(C, -C4) alkyl ammonium, polyhydroxyltetra (C, -C4) alkyl ammonium, dialkylpiperidinium, dialkylpyrrolidinium, dialkylmorpholinium, 10 dialkylthiomorpholinium, dialkylpiperazinium, azepinium, and 1,4-diazabicyclo [2,2,2] octanium.
Even more preferably, D represents a group 3-methylimidazolidinium-1-yl, 3- (2-hydroxyethyl) imidazolidinium-1-yl, 1,2,4-triazolinium-1-yl, 1,2,4-triazolinium-4-yl, N-alkyl (C, -C,) pyridinium-2-yl, N-alkyl (C, -C4) pyridinum-3-yl, N-alkyl (C, -C4) pyridinum-4-yl, N- (2-hydroxyethyl) pyridinum-2-yl, N- (2-hydroxyethyl) pyridinum-3-yl, N- (2-hydroxyethyl) pyridinum-4-yl, pyridinum-1-yl, trtalkyl (C, -C4) ammonium-N-yl, 1-methylpiperidinium-1-yl, 1,4-dimetylpiperazinium-1-yl.
Preferably, A represents an imidazolidinium group, N-alkyl (C, -C4) pyridinium, N- (2-hydroxyethyl) pyridinium, pyridinium, dialkyl (C, -C,) ammonium, 1,4-dimetylpiperazinium-1-yl.
Preferably, B, B, and B2, independently of each other, represent an arm - (CH2 ~, - (CH2) - (CH2 ~., or - (CH2 ~ (CH2) - (CH2 ~.
Among the compounds of formula (I) above, it is very particularly possible to quote - 1,3-bis chloride - [(2-hydroxy-phenylcarbamoyl ~ methyl] -3H-imidazol-1-ium;
SUBSTITUTE SHEET (RULE 26) - 1,3-bis chloride - [(2-hydroxy-4-methyl-phenylcarbamoyl ~ methylj-3H-imidazol-1-ium;
- 1,3-bis chloride - [(2-hydroxy-4-amino-phenylcarbamoyl ~ methyl] -3H-imidazol-1-ium;
- 1,3-bis chloride - [(2-hydroxy-4-acetylamino-phenylcarbamoyl ~ methylJ-3H-imidazol-1-ium;
- 1,3-bis chloride - [(2-hydroxy-4-methoxycarbonylamino-phenylcarbamoyl ~
methyl] -3H-imidazol-1-ium;
- 1,3-bis chloride - [(3-hydroxy-4-acetylamino-phenylcarbamoyl ~ methyl] -3H-imidazol-1-ium;
- 1,3-bis chloride - [(3-hydroxy-4-methoxycarbonylamino-phenylcarbamoyl ~
methyl] -3H-imidazol-1-ium;
- 1,3-bis chloride - [(2-hydroxy-5-chloro-phenylcarbamoyl) -methyl] -3H-imidazol-1-ium;
- 1,3-bis chloride - [(2-hydroxy-4-methyl-5-chioro-phenylcarbamoyl) -methyl] -3H-imidazol-1-ium;
- 1,3-bis chloride - [(2-hydroxy-4-amino-5-chloro-phenylcarbamoylrmethyl] -3H-imidazol-1-ium;
- 1,3-bis chloride - [(2-hydroxy-4-acetylamino-5-chloro-phenylcarbamoylr methyl] -3H-imidazol-1-ium;
- 1,3-bis chloride - [(2-hydroxy-4-methoxycarbonylamino-5-chloro-phenylcarbamoyl ~ methyl] -3H-imidazol-1-ium;
- 1,3-bis chloride - [(3-hydroxy-4-acetylamino-5-chloro-phenylcarbamoyl ~
methyl] -3H-imidazol-1-ium;
- 1,3-bis chloride - [(3-hydroxy-4-methoxycarbonylamino-6-chioro-phenylcarbamoyl} -methyl] -3H-imidazol-1-ium;
- 1,3-bis chloride - [(2-hydroxy-5-methoxy-phenylcarbamoyl ~ -methyl] -3H-imidazol-1-ium;
- 1,3-bis chloride - [(2-hydroxy-4-methyl-5-methoxy-phenylcarbamoyl ~
methyl] -3H-imidazol-1-ium;
- 1,3-bis chloride - [(2-hydroxy-4-amino-5-methoxy-phenylcarbamoyl ~
SUBSTITUTE SHEET (RULE 26) methylj-3H-imidazol-1-ium;
- 1,3-bis chloride - [(2-hydroxy-4-acetylamino-5-methoxy-phenylcarbamoyl) _methyl] -3H-imidazol-1-ium;
- 1,3-bis chloride - [(2-hydroxy-4-methoxycarbonylamino-5-methoxy-phenylcarbamoylrmethylj-3H-imidazol-1-ium;
- 1,3-bis chloride - [(3-hydroxy-4-acetylamino-fi-methoxy-phenylcarbamoyl) -methyl] -3H-imidazol-1-ium;
- 1,3-bis chloride - [(3-hydroxy-4-methoxycarbonylamino-6-methoxy phenylcarbamoyl) -methyl] -3H-imidazol-1-ium;
- 1,3-bis chloride - [(2-hydroxy-fi-amino-phenylcarbamoyl) -methyl] -3H-imidazol-1-ium;
- 1,3-bis chloride - [(2-hydroxy-fi-acetylamino-phenylcarbamoylrméthylj-3H-imidazol-1-ium;
- 1,3-bls chloride - [(2-hydroxy-4, fi-diamino-phenylcarbamoyl) -methyl] -3H-imidazol-1-ium;
- 1,3-bis chloride - [(2-hydroxy-4-acetylamino-6-amino-phenylcarbamoyl) -methylj-3H-imidazol-1-ium;
- 1,3-bis chloride - [(2-hydroxy-3,5-dichloro-4-methyl-phenylcarbamoyl) -methylj-3H-imidazol-1-ium;
- 1,3-bis chloride - [(2-hydroxy-3,5-dichloro-4-amino-phenylcarbamoyl) -methylj-3H-imidazol-1-ium;
- 1,3-bis chloride - [{2-hydroxy-3,5-dichloro-4-acetylamino-phenylcarbamoyl) -methyl] -3H-imidazol-1-ium;
- 1,3-bis chloride - [{2-hydroxy-3,5-dichloro-4-methoxycarbonylamino-phenylcarbamoyl} -methylj-3H-imidazol-1-ium;
- 1,3-bis chloride - [(2-hydroxy-3-acetylamino-phenylcarbamoyl) -methyl] -3H-imidazol-1-ium;
- chloride of 3 - [(2-hydroxy-4-amino-phenyicarbamoyl) -methylj-1 - [(2-hydroxy-4-methyl-phenylcarbamoyl) -methyl] -3H-imidazol-1-ium;
- 3 - [(2-hydroxy-3,5-dichloro-4-methyl-phenylcarbamoyl ~ methylj chloride 1 - [(2-hydroxy-4-methyl-phenylcarbamoyl) -methylj-3H-irnidazol-1-ium;
SUBSTITUTE SHEET (RULE 26) - 1,4-bis chloride - [(2-hydroxy-phenylcarbamoyl ~ methyf) -1-methyl-piperazin-1-ium;
- 1,4-bis chloride - [(2-hydroxy-4-methyl-phenylcarbamoyl ~ methyl] -1-methyl-piperazin-1-ium;
- 1,4-bis chloride - [{2-hydroxy-4-amino-phenylcarbamoyl) -methyl] -1-methyl-piperazin-1-ium;
- 1,4-bis chloride - [(2-hydroxy-4-acetylamino-phenylcarbamoylrmethylJ-1-methyl-piperazin-1-ium;
- 1,4-bis chloride - [(2-hydroxy-4-methoxycarbonylamino-phenylcarbamoyl) -methylj-1-methyl-piperazin-1-ium;
- 1,4-bis chloride - [(3-hydroxy-4-acetylamino-phenylcarbamoyl) -methylj-1-methyl-piperazin-1-ium;
- 1,4-bis chloride - [(3-hydroxy-4-methoxycarbonylamino-phenylcarbamoyl) -methyl] -1-methyl-piperazin-1-ium;
- 1,4-bis chloride - [(2-hydroxy-5-chloro-phenylcarbamoyl ~ methyl] -1-methyl-piperazin-1-ium;
- 1,4-bis chloride - [{2-hydroxy-4-methyl-5-chloro-phenylcarbamoyl) -methyl] -1-methyl-piperazin-1-ium;
- 1,4-bis chloride - [{2-hydroxy-4-amino-5-chloro-phenylcarbamoyl ~ methyl] -1-methyl-piperazin-1-ium;
- 1,4-bis chloride - [{2-hydroxy-4-acetylamino-5-chloro-phenylcarbamoyl) -methylj-1-methyl-piperazin-1-ium;
- 1,4-bis chloride - [(2-hydroxy-4-methoxycarbonylamino-5-chloro-phenylcarbamoyl) -methyl] -1-methyl-piperazin-1-ium;
- 1,4-bis chloride - [(3-hydroxy-4-acetylamino-6-chloro-phenylcarbamoyl ~
methyl] -1-methyl-piperazin-1-ium;
- 1,4-bis chloride - [(3-hydroxy-4-methoxycarbonylamino-6-chloro-phenylcarbamoylrmethylj-1-methyl-piperazin-1-ium;
- 1,4-bis chloride - [(2-hydroxy-5-methoxy-phenylcarbamoylrmethyl] -1-methyl-piperazin-1-ium;
1,4-bis chloride - [(2-hydroxy-4-methyl-5-methoxy-phenylcarbamoyl ~
SUBSTITUTE SHEET (RULE 26) methyl] -1-methyl-piperazin-1-ium;
- 1,4-bis chloride - [(2-hydroxy-4-amino-5-methoxy-phenylcarbamoyl) -methyl] -1-methyl-piperazin-1-ium;
- 1,4-bis chloride - [(2-hydroxy-4-acetylamino-5-methoxy-phenylcarbamoyl) -methyl] -1-methyl-piperazin-1-ium;
- 1,4-bis chloride - [(2-hydroxy-4-methoxycarbonylamino-5-methoxy-phenylcarbamoyl ~ methyl] -1-methyl-piperazin-1-ium;
- 1,4-bis chloride - [(3-hydroxy-4-acetylamino-6-methoxy-phenylcarbamoyl ~ methyl] -1-methyl-piperazin-1-ium;
- 1,4-bis chloride - [(3-hydroxy-4-methoxycarbonylamino-6-methoxy-phenylcarbamoyl) -methyl] -1-methyl-piperazin-1-ium;
- 1,4-bis chloride - [{2-hydroxy-6-amino-phenylcarbamoyl) _methyl] -1-methyl-piperazin-1-ium;
- 1,4-bis chloride - [(2-hydroxy-6-acetylamino-phenylcarbamoyi ~ methyl] -1-methyl-piperazin-1-ium;
- 1,4-bis chloride - [(2-hydroxy-4,6-diamino-phenylcarbamoyl ~ methyl] -1-methyl-piperazin-1-ium;
- 1,4-bis chloride - [(2-hydroxy-4-acetylamino-6-amino-phenylcarbamoyl) -methyl] -1-methyl-piperazin-1-ium;
- 1,4-bis chloride - [(2-hydroxy-3,5-dichloro-4-methyl-phenylcarbamoyl) -methyl] -1-methyl-piperazin-1-ium;
- 1,4-bis chloride - [{2-hydroxy-3,5-dichloro-4-amino-phenyicarbamoyl) -methyl] -1-methyl-piperazin-1-ium;
- 1,4-bis chloride - [{2-hydroxy-3,5-dichloro-4-acetylamino-phenylcarbamoyl) -methyl] -1-methyl-piperazin-1-ium;
- 1,4-bis - [(2-hydroxy-3,5-dichloro-4-methoxycarbonylamino-) chloride phenylcarbamoyl) -methyl] -1-methyl-piperazin-1-ium;
- 1,4-bis chloride - [(2-hydroxy-3-acetylamino-phenylcarbamoyl) -methyl] -1-methyl-piperazin-1-ium;
and their addition salts with an acid.
SUBSTITUTE SHEET (RULE 26) The compounds of formula (I) in accordance with the invention can be prepared according to methods well known in the state of the art and described by example in patent applications or patents FR-A-1,596,879;
BE 816 674; EP 0 579 204; DE 2 84fi 931; JP-54-115 230; GB 2,070,000;
S DE 3,027,128; EP 0 065 874; EPO 115 194; EP 0 079 141; EP 0 081 321;
DE 3,246,238; EP 0 168 729; DE 3,414,051; JP-59-059656; FR-A-2,575,470;
EP 0 193 051; JP-63-208562; JP-62-173469; JP-62-108859; JP-62-173469;
DD253997; DE 3,641,825, JP-63-208562; DE 3,621,215; JP-01-249739;
JP-64-002045; JP-02-255674; JP-01-032261; JP-02-255674; EP 0 608 896, WO 94/19316; JP-09-169705; EP 0 790 240; as well as in the documents Res. Discl. (1981), 202, 76-8; Synthesis (1982), 940-2; Res. Discl. (1983), 235, 352-3; Res. Discl. (1984), 247, 554-6; Res. Discl. (1985), 251, 134-9;
Chem.
Ind. (Dekker) (1992), 47 (fatal. Org. React.), 147-51; and J. Med. Chem.
(1998), 41, 4062-79.
Another subject of the invention is (use of the compounds of formula (I) in accordance with (invention as coupler for the oxidation dye of fibers keratin, and in particular human keratin fibers such as the hair.
A subject of the invention is also a composition for dyeing.
oxidation keratin fibers and in particular human keratin fibers such hair, characterized by the fact that it includes, in a medium suitable for dyeing, at least one compound of formula (I) in accordance with (invention and at least one oxidation base.
The compound or compounds of formula (I) in accordance with (invention and / or the or their salts of addition with an acid preferably represent from 0.0005 to 12% by weight about the total weight of the dye composition, and even more preferably from 0.005 to 6% by weight approximately of this weight.
SUBSTITUTE SHEET (RULE 26) The nature of the oxidation base (s) that can be used in the dye composition according to the invention is not critical. They are of preferably chosen from the oxidation bases conventionally used in oxidation dye and among which there may be mentioned in particular the para-phenylenediamines, bis-phenylalkylenediamines, para-aminophenols, ortho-aminophenols and heterocyclic bases.
Among the paraphenylenediamines, there may be mentioned more particularly as for example, paraphenylenediamine,! a paratoluylenediamine, 2-chloro paraphenylenediamine, 2,3-dimethyl paraphenylenediamine, 2,6-dimethyl paraphenylenediamine, 2,6-diethyl paraphenylenediamine, 2,5-dimethyl paraphenylenediamine, N, N-dimethyl paraphenylenediamine, N, N-diethyl paraphenylenediamine, N, N-dipropyl paraphenylenediamine, 4-amino N, N-diethyl 3-methyl aniline, N, N-bis- (~ i-hydroxyethyl) IS paraphenylenediamine, 4-N, N-bis- (~ 3-hydroxyethyl) amino 2-methyl aniline, the 4-N, N-bis - ((i-hydroxyethyl) amino 2-chloro aniline, 2- (3-hydroxyethyl paraphenylenediamine, 2-fluoro paraphenylenediamine, 2-isopropyl paraphenylenediamine, N- (~ -hydroxypropyl) paraphenylenediamine, 2-hydroxymethyl paraphenylenediamine, N, N-dimethyl 3-methyl para-phenylenediamine, N, N- (ethyl, (i-hydroxyethyl) para-phenylenediamine, N- (~ i, Y-dihydroxypropyl) paraphenylenediamine, N- (4'-aminophenyl) paraphenylenediamine, N-phenyl paraphenylenediamine, 2- (i-hydroxyethyloxy paraphenylenediamine, 2- ~ -acetylaminoethyloxy paraphenylenediamine, N- (~ i-methoxyethyl) paraphenylenediamine, and their addition salts with an acid.
Among the paraphenylenediamines mentioned above, all are preferred particularly paraphenylenediamine, paratoluylenediamine, 2-isopropyl paraphenylenediamine, 2- ~ i-hydroxyethyl paraphenylenediamine, 2- (i-hydroxyethyloxy paraphenylenediamine, 2,6-dimethyl paraphenylenediamine, 2,6-diethyl paraphenylenediamine, 2,3-dimethyl SUBSTITUTE SHEET (RULE 26) para-phenylenediamine, N, N-bis- (~ i-hydroxyethyl) para-phenylenediamine, 2-chloro paraphenylenediamine, 2-p-acetylaminoethyloxy paraphenylenediamine, and their addition salts with an acid.
Among the bis-phenylalkylenediamines, mention may be made more particularly of:
title for example, N, N'-bis- (~ i-hydroxyethyl) N, N'-bis- (4'-aminophenyl) 1,3-diamino propanol, N, N'-bis- (~ -hydroxyethyl) N, N'-bis- (4'-aminophényi) ethylenediamine, N, N'-bis- (4-aminophenyl) tetramethylenediamine, N, N'-bis- (~ -hydroxyethyl) N, N'-bis- (4-aminophenyl) tetramethylenediamine, the N, N'-bis- (4-methyl-aminophenyl) tetramethylenediamine, N, N'-bis- (ethyl) N, N'-bis- (4'-amino, 3'-methylpheny!) Ethylenediamine, 1,8-bis- (2,5-diaminophenoxy) -3,5-dioxaoctane, and their addition salts with an acid.
Among the para-aminophenols, there may be mentioned more particularly as example, para-aminophenol, 4-amino 3-methyl phenol, 4-amino 3-fluoro phenol, 4-amino 3-hydroxymethyl phenol, 4-amino 2-methyl phenol, 4-amino 2-hydroxymethyl phenol, 4-amino 2-methoxymethyl phenol, 4-amino 2-aminomethyl phenol, 4-amino 2- (~ i-hydroxyethyl aminomethyl) phenol, 4-amino 2-fluoro phenol, and their addition salts with an acid.
Among the ortho-aminophenols, there may be mentioned more particularly as for example, 2-amino phenol, 2-amino 5-methyl phenol, 2-amino 6-methyl phenol, 5-acetamido 2-amino phenol, and their acid addition salts.
Among the heterocyclic bases, there may be more particularly mentioned as for example, pyridine derivatives, pyrimidine derivatives and derivatives pyrazolics.
Among the pyridine derivatives, mention may be made more particularly of compounds described for example in patents GB 1,026,978 and GB 1,153,196, as the SUBSTITUTE SHEET (RULE 26) 2,5-diamino pyridine, 2- (4-methoxyphenyl) amino 3-amino pyridine, 2,3-diamino 6-methoxy pyridine, la 2 - (/ 3-methoxyethyl) amino 3-amino 6-methoxy pyridine, 3,4-diamino pyridine, and their acid addition salts.
Among the pyrimidine derivatives, mention may be made more particularly of compounds described for example in German patents DE 2,359,399 or Japanese JP 88-169 571 and JP 91-10659 or patent application WO 96115765, such as 2,4,5,6-tetra-aminopyrimidine, 4-hydroxy 2,5,6-triaminopyrimidine, 2-hydroxy 4,5,6-triaminopyrimidine, 2,4-dihydroxy 5,6-diaminopyrimidine, the 2,5,6-triaminopyrimidine, and pyrazolo-pyrimidine derivatives such as those mentioned in patent application FR-A-2 750 048 and among which are may include pyrazolo- [1,5-a] -pyrimidine-3,7-diamine; 2,5-dimethyl pyrazolo- [1,5-a] -pyrimidine-3,7-diamine; pyrazolo- [1,5-a] -pyrimidine-3,5-diamine; 2,7-dimethyl pyrazolo- [1,5-a] -pyrimidine-3,5-diamine; 3-amino pyrazolo- [1,5-a] -pyrimidin-7-ol; 3-amino pyrazolo- [1,5-a] -pyrimidin-5-ol;
the 2- (3-amino pyrazolo- [1,5-a] -pyrimidin-7-ylamino) -ethanol, 2- (7-amino pyrazolo- [1,5-a] -pyrimidin-3-ylamino ~ ethanol, 2 - [(3-amino-pyrazolo [1,5-a] pyrimidin-7-yl) - (2-hydroxy-ethyl ~ amino] -ethanol, 2 - [(7-amino-pyrazolo [1,5-a] pyrimidin-3-yl ~ - (2-hydroxy-ethyl) -amino] -ethanol, 5,6-dimethyl pyrazolo-[1.5-a] -pyrimidine-3,7-diamine, 2,6-dimethyl pyrazolo- [1,5-a] -pyrimidine-3,7-diamine, la 2, 5, N 7, N 7-tetramethyl pyrazolo- [1,5-a] -pyrimidine-3,7-diamine, and their addition salts and their tautomeric forms, when a balanced tautomeric and their acid addition salts.
Among the pyrazole derivatives, mention may more particularly be made of compounds described in patents DE 3 843 892, DE 4 133 957 and patent applications WO 94/08969, WO 94/08970, FR-A-2 733 749 and DE 195 43 988 like the 4,5-diamino 1-methyl pyrazole, 3,4-diamino pyrazole, 4,5-diamino 1- (4'-chlorobenzyl) pyrazole, 4,5-diamino 1,3-dimethyl pyrazole, 4,5-diamino 3-methyl 1-phenyl pyrazole, 4,5-diamino 1-methyl 3-phenyl pyrazole, 4-amino 1,3-dimethyl 5-hydrazino pyrazole, 1-benzyl 4,5-diamino SUBSTITUTE SHEET (RECLE 26) 3-methyl pyrazole, 4,5-diamino 3-tert-butyl 1-methyl pyrazole, 4,5-diamino 1-tert-butyl 3-methyl pyrazole, 4,5-diamino 1- (~ i-hydroxyethyl) 3-methyl pyrazole, 4,5-diamino 1-ethyl 3-methyl pyrazole, 4,5-diamino 1-ethyl 3- (4'-methoxyphenyl) pyrazole, 4,5-diamino 1-ethyl 3-hydroxymethyl pyrazole, 4,5-diamino 3-hydroxymethyl 1-methyl pyrazole, 4,5-diamino 3-hydroxymethyl 1-isopropyl pyrazole, 4,5-diamino 3-methyl 1-isopropyl pyrazole, 4-amino 5- (2'-aminoethyl) amino 1,3-dimethyl pyrazoie, 3,4,5-triamino pyrazole, 1-methyl 3,4,5-triamino pyrazole, 3,5-diamino 1-methyl 4-methylamino pyrazole, 3,5-diamino 4 - {(3-hydroxyethyl) amino 1-methyl pyrazole, and their addition salts with an acid.
According to (invention, the dye compositions containing one or more paraphenylenediamines and / or one or more oxidation bases heterocyclics are particularly preferred.
The oxidation base (s) preferably represent from 0.0005 to 12% by weight about the total weight of the dye composition, and even more preferably from 0.005 to 6% by weight approximately of this weight.
The dye composition in accordance with the invention may also contain, in more of the compound (s) of formula (I) above, one or more couplers which can be chosen from the couplers used classic in oxidation dye and among which we can especially quote the metaphenylenediamines, meta-aminophenols, metadiphenols and heterocyclic couplers such as, for example, indole derivatives, indolinic derivatives, pyridine derivatives and pyrazolones, and their salts addition with an acid.
These couplers are more particularly chosen from 2-methyl 5-amino phenol, 5-N - {(i-hydroxyethyl) amino 2-methyl phenol, 3-amino phenol, 1,3-dihydroxy benzene, 1,3-dihydroxy 2-methyl benzene, 4-chloro SUBSTITUTE SHEET {RULE 26) WO 00/43368 PCf / FR00 / 00143 1,3-dihydroxy benzene, 2,4-diamino 1- (~ -hydroxyethyloxy) benzene, 2-amino 4- (~ i-hydroxyethylamino) 1-methoxy benzene, 1,3-diamino benzene, 1,3-bis- (2,4-diaminophenoxy) propane, sesamol, fa-naphthol, 6-hydroxy indole, 4-hydroxy indoie, 4-hydroxy N-methyl indole, 6-hydroxy indoline, 5 2,6-dihydroxy 4-methyl pyridine, 1-H 3-methyl pyrazole 5-one, 1-phenyl 3-methyl pyrazole 5-one, and their addition salts with an acid.
When present, these additional couplers preferably represent from 0.0001 to 10% by weight approximately of the total weight of the dye composition and 10 more preferably still from 0.005 to 5% by weight approximately of this weight.
In general, the acid addition salts usable in the framework of the dye compositions of (invention (compounds of formula (I), oxidation bases and additional couplers} are chosen in particular from 15 hydrochlorides, hydrobromides, sulfates, citrates, succinct, the tartrates, lactates and acetates.
The medium suitable for dyeing (or support) generally consists through of Skin or by a mixture of water and at least one organic solvent to

20 to solubilize the compounds which would not be sufficiently soluble in Skin.
Mention may, for example, be made, as organic solvent, of alkanols.
lower in C, -C4, such as fethanol and fisopropanol; glycerol; glycols and ethers of glycols such as 2-butoxyethanol, propylene glycol, monomethyl ether propylene glycol, monoethyl ether and monomethyl ether of diethylene glycol, 25 as well as aromatic alcohols such as (benzyl alcohol or phenoxyethanol, analogues and their mixtures.
The solvents may be present in proportions preferably between 1 and 40% by weight approximately relative to the total weight of the 30 dye composition, and even more preferably between 5 and 30%
in weight approx.
SUBSTITUTE SHEET (RULE 26) The pH of the dye composition in accordance with the invention is generally included enta: 3 and 12 approximately, and preferably between 5 and 11 approximately. He can be adjusted to the desired value using acidifying or basifying agents usually used in dyeing keratin fibers.
Among the acidifying agents, there may be mentioned, by way of example, the acids minerals or organic like (hydrochloric acid, (orthophosphoric acid, acid sulfuric, carboxylic acids like acetic acid, acid tartaric, citric acid, lactic acid, sulfonic acids.

Among the basifying agents, there may be mentioned, by way of example, (ammonia, the alkaline carbonates, alkanolamines such as mono-, di- and triethanolamines and their derivatives, sodium hydroxides or potassium and the compounds of formula (V) below ~ "25 / N'WN ~ N) Laugh in which W is a propylene residue substituted or unsubstituted by a hydroxyl group or an alkyl radical in C, -CB; Rte, R24, R ~ and Rte, identical or different, represent a hydrogen atom, an alkyl radical C, -Ce or hydroxyalkyl C, -CB.
The oxidation dye compositions according to (invention can also contain at least one direct dye, in particular to modify the nuances or enrich them with reflections.
The dye composition in accordance with (the invention may also include various adjuvants conventionally used in dyeing compositions hair, such as anionic, cationic, non-surface active agents ionic, amphoteric, zwitterionic or mixtures thereof, polymers REPLACEMENT SHEET (RULE 2â) anionic, cationic, nonionic, amphoteric, zwitterionic or their mixtures, mineral or organic thickening agents, agents antioxidants, penetrating agents, sequestering agents, perfumes, tampons, dispersing agents, conditioning agents such as for example volatile or non-volatile, modified or no modified, film-forming agents, ceramides, preservatives, opacifying agents.
Of course, (man of fart will take care to choose this or these possible compounds complementary in such a way that the advantageous properties attached intrinsically to the oxidation dye composition in accordance with the invention are not, or not substantially, altered by the addition (s) considered.
The dye composition according to (invention can be in forms various, such as liquids, creams, gels, or any another suitable form for dyeing keratin fibers, and especially human hair.
The invention also relates to a process for dyeing oxidation of fibers keratin and in particular human keratin fibers such as hair using the dye composition as defined previously.
According to this process, at least one composition is applied to the fibers dye as defined above, the color being revealed at pH
acid, neutral or alkaline using an oxidizing agent which is added just when of (use in the dye composition or which is present in a composition oxidative applied simultaneously or sequentially.
SUBSTITUTE SHEET (RULE 26) WO 00/43368 PCTlFR00 / 00193 According to a preferred embodiment of the dyeing process of the invention, the composition is preferably mixed at the time of (use, the composition dye described above with an oxidizing composition containing, in a medium suitable for dyeing, at least one oxidizing agent present in a enough to develop a color. The mixture obtained is then applied to the keratin fibers and left to stand for 3 to 50 minutes approximately, preferably 5 to 30 minutes approximately, after which one rinses, one wash with shampoo, rinse again and dry.
The oxidizing agent can be chosen from conventionally oxidizing agents used for oxidation dyeing of keratin fibers, and among which one may include hydrogen peroxide, urea peroxide, metal bromates alkalis, persalts such as perborates and persulfates, and enzymes such as peroxidases, laccases, tyrosynases and oxidoreductases IS among which we can in particular mention the pyranose oxidases, the glucose oxidases, glycerol oxidases, lactate oxidases, pynrvate oxidases, and uricases.
The pH of the oxidizing composition containing (oxidizing agent as defined above is such that after mixing with the dye composition, the pH of the resulting composition applied to keratin fibers varies from preference between 3 and 12 approximately, and even more preferably between 5 and 11. It is adjusted to the desired value using acidifying or basifying agents usually used in dyeing keratin fibers and such as defined previously.
The oxidizing composition as defined above can also contain various adjuvants conventionally used in dyeing compositions hair and as defined above.
SUBSTITUTE SHEET (RULE 26) WO 00/43368 PCT / P'R00 / OOL43 The composition which is finally applied to the keratin fibers can is present in various forms, such as in the form of liquids, creams, gels, or any other suitable form to achieve a dyeing keratin fibers, and in particular human hair.
Another object of the invention is a device with several compartments or "kit"
dye or any other multi-pack system compartments of which a first compartment contains the composition dye as defined above and a second compartment contains the oxidizing composition as defined above. These devices can be equipped with a means for delivering the mixture to the hair desired, such as the devices described in patent FR-2,586,913 in the name of the plaintiff.
The following examples are intended to illustrate (invention.

SUBSTITUTE SHEET (RULE 26) WO 00/43368 PCT / FIt00 / 00143 PREPARATION EXAMPLE: Synthesis of. 1,3-bis chloride - [(2 ~
hydroxy-4-methyl-phenylcarbamoyl) -methyl] -3H-imidazol-1-ium.
H CI_ HH
N / ~. NOT
I ¿¿~ ~ f '~ ¿~ ¿I
io 0 a) Preparation of 2-chloro-N- (2-hydroxy-4-methyl-pheny ~ acetamide To a solution of 83 g of 2-hydroxy-4-methylaniline (0.674 mole) in 2.5 liter of tetrahydrofuran, with stirring and under an inert atmosphere, were added 10 95 ml of triethylamine (0.674 mole), then after 30 minutes we added drop at drop a solution of 54 ml of chloroacetyl chloride (0.678 mole) in 60 ml of tetrahydrofuran, maintaining the temperature at 25-27 ° C. The middle reaction was stirred at room temperature for 4 hours, filtered through sintered glass and the mineral salts were rinsed with 500 ml of tetrahydrofuran.
15 The combined organic phases were poured onto 3 liters of ice water under agitation. The precipitate formed was drained, washed twice with 600 ml of water and once with pentane, and dried under vacuum to constant weight to give 99 g of 2-chloro-N- (2-hydroxy-4-methyl-phenyl ~ acetamide in the form of a beige powder, with a yield of 74%.
b) Preparation of 1,3-bis chloride - [(2-hydroxy-4-methyl-phenylcarbamoyl ~
methyl] -3H-imidazol-1-ium A solution of 2-chloro-N- (2-hydroxy-4-methyl-phenyl ~ acetamide (6 g, 30 mmoies) obtained above at (previous step, and imidazole (680 mg, 10 mmol) in 40 ml of 1,2-dimethoxy-ethylene was heated to reflux for 48 hours. The precipitate formed was drained, washed twice with 1,2-dimethoxy-ethylene. The 2 g of white powder thus obtained were put suspended in 100 ml of water. The pH of the reaction medium was brought to 7.0 SUBSTITUTE SHEET (RULE 26) by adding a sodium hydroxide solution (10%, then 0.1%). The precipitate was wrung and washed with a minimum of water, then stirred for one hour in 800 ml of water. The suspension was filtered. The aqueous filtrate was concentrated under vacuum and vacuum dried to constant weight to give 0.5 g of chloride 1,3-bis - [(2-hydroxy-4-methyl-phenylcarbamoyl ~ methylJ-3H-imidazol-1-ium in the form of a white powder melting at 232 ° C, and spectroscopy of cation mass: m / z = 395 was in accordance with the expected product.
DYEING EXAMPLES

The following dye compositions were prepared (contents in grams) 1,3-bis - [(2-hydroxy-4-methyl-chloride) phnylcarbamoyl ~ methyl] -3H-imidazol-1-ium 1.30 1.30 1.30 (composed of formula (I)) Paraphnylnediamine (oxidation base) 0.324 - -Pyrazolo- [1,5-a] -pyrimidine-3,7-diamine, - 0,666 -2HCI (base oxidation) N, N-bis hydroxythyl paraphnylnediamine, 2HCI- - 0.882 (oxidation base) Common dye support n1 (*) (*) (*) Demineralized water qs 100 100 100 ggg IS

(*) Common dye support n ° 1 - Benzyüque alcohol 2 ~ 0 g - Polyethylene glycol with 6 moles of ethylene oxide 3.0 g SUBSTITUTE SHEET (RULE 26) - Ethanol at 96 ° 20.0 - Alkyl (C8-C, o) polyglucoside in aqueous solution at 60% of active ingredient (AM), buffered with ammonium citrate, sold under the name ORAMIX CG 110 ~ by the SEPPIC 6.0 g - Ammonia at 20% NH3 10.0 g - Sodium metabisulfite with 35% active ingredient 0.228 g - Pentasodium salt of diethylenetriaminopentacetic acid 1.1 g At the time of use, weights were mixed for each above dye compositions with hydrogen peroxide solution at 20 volumes (6% by weight) of pH 3.
The mixture obtained was applied to locks of natural gray hair to 90% white for 30 minutes. The locks were then rinsed, washed with a standard shampoo, rinsed again and then dried.
The shades obtained are shown in the table below ---.
EXAMPLE dye pH Shade obtained 1 10 t 0.2 Light ash ash slightly blue 2 10 t 0.2 Iris blonde 3 10 t 0.2 Matt blue SUBSTITUTE SHEET (RULE 26)

Claims (34)

1. Cationic 2-acylaminophenols of the following formula (I) and their salts addition with an acid:

in which:
- group A represents a group represented by group D
as defined below;
- B1 and B2, independently of each other, represent a group represented by group B as defined below;
- k, l and m are integers, which can independently take the each other, the value 0 or 1; the sum k + l + m being different from zero ;
- W1 and W2 represent, independently of each other, a group W
represented by the following formula (II):

formula (II) in which:
~ R1 represents a hydrogen atom; a group Z as defined below; a radical comprising from 1 to 15 carbon atoms, linear or branched (the branch or branches that can form one or more cycles carbonaceous with 3 to 7 links), which may contain one or more double bonds and/or one or more triple bonds (the said bonds doubles possibly leading to aromatic groups), of which one or more carbon atoms may be replaced by an atom oxygen, nitrogen, or sulfur or by an SO2 group, and whose carbon atoms can, independently of each other, be substituted by one or more halogen atoms; it being understood that said SO2 group is not directly connected to the nitrogen atom in position 7 bearing the radical R1; said radical R1 not comprising a peroxide bond or diazo, nitro or nitroso radicals; it being understood that the radical R1; not does not represent a hydroxy, amino, thio, alkoxy and alkylthio radical.
~ R2 represents a hydrogen atom; a group Z as defined below; a radical comprising from 1 to 20 carbon atoms, linear or branched (the branch or branches that can form one or more carbon rings having 3 to 7 links), which may contain one or more bonds double bonds and/or one or more triple bonds (the said double bonds possibly leading to aromatic groups), and of which one or several carbon atoms can be replaced by one atom oxygen, nitrogen, or sulfur or by an SO2 group, and whose carbon atoms can, independently of each other, be substituted by one or more halogen atoms; said radical R2 ne containing no peroxide bond or diazo, nitro or nitroso radicals; and it being understood that R2 cannot represent a hydroxyl or thio radical;
~ the radicals R1 and R2 can, in addition, be connected to form a ring saturated or unsaturated with 5 to 7 members, consisting of carbon, of nitrogen, oxygen, sulfur and/or by C=O group, each member being substituted or unsubstituted by 1 or 2 identical or different R radicals, R
being a C1-C6 alkyl radical, linear or branched (the branch or branches which can then form one or more cycles comprising 3 to 6 members), which may contain one or more double bonds and/or one or more triple bonds (said double bonds possibly leading to aromatic groups), and of which one or more carbon atoms may be replaced by an oxygen, nitrogen, or sulfur atom or by an SO2 group, and whose carbon atoms can, independently of each other, be substituted by one or more halogen atoms; said radical R not comprising a peroxide bond nor diazo, nitro or nitroso radicals;
~ R3, R4 and R5, identical or different, represent a hydrogen atom or halogen; a group Z as defined below; a radical comprising from 1 to 20 carbon atoms, linear or branched (the branch or branches can then form one or more rings comprising 3 to 7 members), which may contain one or more double bonds and/or one or more triple bonds (said double bonds possibly leading to aromatic groups), and of which one or more carbon atoms may be replaced by an oxygen, nitrogen, or sulfur atom or by an SO2 group, and whose carbon atoms can, independently of each other, be substituted by one or more halogen atoms; said radicals R3, R4 and R5 not comprising any peroxide bond or of diazo, nitro or nitroso radicals; and it being understood that R5 cannot represent a hydroxyl, thio, amino radical or a group substituted or unsubstituted sulfonylamino; and it being understood that the radicals R3, R4 and R5 cannot be linked to the benzene ring of formula (II) by an -NH-NH- bond;
radicals R1 and R3 can further be joined to form a saturated ring 6 to 7 membered, consisting of carbon, nitrogen, oxygen, sulfur and/or by C=O group, each member being substituted or not substituted by 1 or 2 radicals R, identical or different, R having the same meanings than those indicated above; said radical R
containing no peroxide bond or diazo, nitro or nitroso radicals;
radicals R2 and R3 can also be joined to form a ring saturated with 5 to 7 members, consisting of carbon, nitrogen, oxygen, sulfur and/or by C=O group, each member being substituted or unsubstituted by 1 or 2 radicals R, identical or different, R having the same meanings as those indicated above; said radical R
containing no peroxide bond or diazo, nitro or nitroso radicals;
~ Y represents a hydrogen or halogen atom; an -OR6 group, -SR6 or -NH-SO2R6 in which R6 represents a C1-C6 alkyl radical, linear or ramified (the ramification(s) then being able to form one or more than one 3- to 6-membered ring), substituted or unsubstituted by one or more radicals chosen from the group consisting of an atom halogen, hydroxy, C1-C4 alkoxy, amino and aminoalkyl C1-C4; a phenyl radical substituted or unsubstituted by one or two radicals chosen from the group consisting of a C1-C4 alkyl radical, trifluoromethyl, carboxy, C1-C4 alkoxycarbonyl, halogen, hydroxy, C1-C4 alkoxy, amino, and amino C1-C4 alkyl; or a benzyl radical; and it being understood that Y cannot represent -NH-SO2R6 when R3 represents a hydroxyl radical;
~ Z is a cationic group represented by the following formula (IV):
in which:
- B represents a radical containing 1 to 15 carbon atoms, linear or ramified (the ramification(s) then being able to form one or more rings with 3 to 7 links), which may contain one or more double bonds and/or one or more triple bonds, said bonds doubles possibly leading to aromatic groups, and one or more carbon atoms of which may be replaced by a oxygen, nitrogen, or sulfur atom or by an SO2 radical; and one of which or more carbon atoms may, independently of each other others, be substituted by one or more halogen atoms or by one or several Z groups; said radical B having no bond peroxide or diazo, nitro or nitroso radicals;
- D is chosen from the cationic groups of formulas (V) and (VI) following:
in which :
- the radical B is linked to the group D by any of the atoms of the radical D;
- n and p can, independently of each other, take the value 0 or 1;
- when n = 0, then the group of formula (VI) can be linked to the compound of formula (II) directly via the ammonium nitrogen atom quaternary, in place of the radical R10.

- Z1, Z2, Z3, and Z4, independently of each other, represent a oxygen atom; a sulfur atom; a substituted nitrogen atom or unsubstituted by an R11 radical; or a substituted carbon atom or unsubstituted by one or two identical or different R11 radicals;
- Z5 represents a nitrogen atom; or a substituted carbon atom or unsubstituted by an R11 radical;
- Z6 can take the same meanings as indicated below for the radical R11, it being understood that Z6 is different from an atom hydrogen;
the radicals Z1 or Z5 can, in addition, form with Z6 a saturated cycle or unsaturated with 5 to 7 members, each member being substituted or unsubstituted by one or two identical or different R11 radicals;
- R11 represents a hydrogen atom; a Z group; a radical containing from 1 to 10 carbon atoms, linear or branched, which can contain one or more double bonds and/or one or more bonds triple bonds, said double bonds possibly then being able to lead to aromatic groups, and of which one or more carbon atoms can be replaced by an oxygen, nitrogen or sulfur atom, or by an SO2 group, and of which one or more carbon atoms may, independently of each other, be substituted by one or several halogen atoms; said radical having no bond peroxide or diazo, nitro or nitroso radicals;
two of the adjacent radicals Z1, Z2, Z3, Z4 and Z5 can additionally form a cycle comprising 5 to 7 links, each link being independently represented by a substituted or unsubstituted carbon atom substituted by one or two identical or different R11 radicals; an atom nitrogen substituted or unsubstituted by an R11 radical; an atom oxygen; or a sulfur atom;
- R7, R8, R9, and R10, identical or different, have the same meanings than those indicated above for the radical R11;
the radicals R7, R8 and R9 can also form, two by two with the quaternary nitrogen atom to which they are attached, one or more saturated cycles comprising from 5 to 7 members, each member being independently represented by a substituted or unsubstituted carbon atom substituted by one or two identical or different R11 radicals; an atom nitrogen substituted or unsubstituted by an R11 radical; an atom oxygen; or a sulfur atom;
- X- represents an organic or inorganic anion;
Being heard that:
- the B1 radical is linked to the A group by any of the atoms of the radical A;
- when k = 0, then group A can be linked to group W1 directly by the nitrogen atom of the quaternary ammonium, instead of the radical R10;
- the B2 radical is linked to the A group by any of the atoms of the radical A;
- when m = 0, then the group A of formula (VI) can be linked to the group W2 directly by the nitrogen atom of the quaternary ammonium, to the place of the radical R10.
- the group B, of formula (I) is connected to an atom of the group W1 and that this atom is identified by an asterisk (*) on the skeleton of W1 represented by formula (III) defined below;

- the B2 group is linked to an atom of the W2 group and that this atom is identified by an asterisk (*) on the skeleton of W2 represented by the formula (III) defined below;
- when k + l = 0, then W1 and/or W2 and/or B2 contain at least one Z-grouping - when l + m = 0, then W1 and/or W2 and/or B1 contain at least one Z-grouping - when l = 1, then k and m, independently of each other, can take the values 0 and 1. 2. Compounds according to claim 1, characterized in that R1 designates a hydrogen atom, a radical Z; a group A1 consisting of a radical C1-C8 alkyl, linear or branched, which may carry one or two doubles bindings or a triple bond, be substituted or unsubstituted by a group selected among an A2 group, an A4 group, and an A5 group, be substituted or unsubstituted by one or two groups, identical or different, chosen from N-alkyl(C1-C3)amino groups, N-alkyl(C1-C3)-N-alkyl(C1-C3)amino, alkoxy(C1-C6), oxo, alkoxycarbonyl, acyloxy, amide, acylamino, ureyl, sulfoxy, sulfonyl, sulfonamido, sulfonylamino, bromo, cyano, carboxy, and be substituted or unsubstituted by a or more hydroxyl, fluoro or chloro groups; A2 consisting of aromatic group of phenyl or naphthyl type, which may be substituted or unsubstituted by one to three groups, identical or different, chosen among methyl, trifluoromethyl, ethyl, isopropyl, butyl, pentyl, fluoro, chloro, bromo, methoxy, trifluoromethoxy, ethoxy, propyloxy, acetyloxy, acetyl, and cyano; A3 consisting of a chosen heteroaromatic group among furanyl, thiophenyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, isoxazolyl, isothiazolyl, pyrazolyl, pyrazoltriazolyl, pyrazololmidazolyl, pyrrolotriazolyl, pyrazolopyrimidyl, pyrazolopyridyl, pyridyl, pyrimidyl, benzoimidazolyl, benzoxazolyl, benzothiazolyl, indolyl, indolidinyl, isoindolyl, indazolyl, benzotriazolyl, quinolinyl, benzoimidazolyl, benzopyrimidyl, said groups being substituted or unsubstituted by 1 to 3 radicals chosen from the radicals alkyl C1-C4, linear or branched, C1-C4 monohydroxyalkyl, polyhydroxyalkyl in C2-C4, carboxy, alkoxycarbonyl, halogen, amido, amino and hydroxy; A4 consisting of a C3-C7 cycloalkyl radical, a norbornanyl radical, wearing or not a double bond and substituted or unsubstituted by 1 or 2 radicals chosen from linear or branched C1-C4 alkyl radicals, monohydroxyalkyl C1-C4 polyhydroxyalkyl C2-C4, carboxy, alkoxycarbonyl, halogen, amido, amino and hydroxy; or A5 consisting of a heterocycle chosen from cycles by dihydrofuranyl, tetrahydrofuranyl, butyrolact-one-yl, dihydrothiophenyl, tetrahydrothiophenyl, tetrahydrothiophen-one-yl, iminothiolane, dihydropyrrolyl, pyrrolidinyl, pyrrolidin-one-yl, imidazolidin-one-yl, imidazolidinthione-yl, oxazolidinyl, oxazolidin-one-yl, oxazolanethione, thiazolidinyl, isothiazol-one-yl, mercaptothiazolinyl, pyrazolidin-one-yl, iminothiolane, dioxolanyl, pentalactone, dioxanyl, dihydropyridinyl, piperidinyl, pentalactam, morpholinyl, pyrazoli(di)nyl, pyrimi(di)nyl, pyrazinyl, piperazinyl and azepinyl; said groups A1, A2 A3, A4 and A5 being optionally separated from the nitrogen located in position 7 on which is fixed ie radical, R1 by a group - (CO) -. 3. Compounds according to claim 1 or 2, characterized in that R1 represents a hydrogen atom; a methyl, ethyl, isopropyl radical, allyl, phenyl, benzyl, fluorobenzyl, hydroxybenzyl, difluorobenzyl, trifluorobenzyl, chlorobenzyl, bromobenzyl, methoxybenzyl, dimethoxybenzyl, (trifluoromethoxy)benzyl, 3,4-methylenedioxybenzyl, 6-chloropiperonyl, 4-methylthiobenzyl, 4-methylsulfonylbenzyl, 4-acetylaminobenzyl, 4-carboxybenzyl, 1-naphthomethyl, 2-naphthomethyl;
or a 2-hydroxyethyl, 2-methoxyethyl or 2-ethoxyethyl group. 4. Compounds according to any one of the preceding claims, characterized in that R2 denotes a hydrogen atom, a group amino; a Z group; a group A1, A2, A3, A4 or A5 as defined at of claim 2, optionally separated from the carbon (in position 8) of the amide function of the compound of formula (II) with an -O-, -NH group, or -NAlkyl(C1-C3). 5. Compounds according to claim 4, characterized in that R2 denotes of preferably a Z group; a radical chosen from the group (G1) consisting by a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, isopentyl, neopentyl, hexyl; cyclopropyl, cyclobutyl, cyclopentyl, cyclopentylmethyl, 3-cyclopentyl-propyl, cyclohexyl, 2-cyclohexyl-ethyl, norbornan-2-yl, vinyl, 1-methylvinyl, 2-methylvinyl, 2,2-dimethylvinyl, allyl, 3-butenyl; phenyl, methylphenyl, dimethylphenyl, 2,4,6-trimethylphenyl, 4-ethylphenyl, (trifluoromethyl)phenyl, hydroxyphenyl, methoxyphenyl, ethoxyphenyl, acetoxyphenyl, (trifluoromethoxy)phenyl, aminophenyl, 4-dimethylaminophenyl, fluorophenyl, difluorophenyl, fluoro(trifluoromethyl)phenyl, chlorophenyl, dichlorophenyl, bromophenyl, naphth-1-yl, naphth-2-yl, (2-methoxy)naphth-1-yl, benzyl, 4'-methoxybenzyl, 2',5'-dimethoxybenzyl, 3',4'-dimethoxybenzyl, 4'-fluorobenzyl, 4'-chlorobenzyl, phenethyl, 2-phenylvinyl, (1-naphthyl)methyl, (2-naphthyl)methyl; tetrahydrofuran-2-yl, furan-2-yl, 5-methyl-2-(trifluoromethyl)furan-3-yl, 2-methyl-5-phenylfuran-3-yl, thiophene-2-yl, (thiophene-2-yl)methyl, 3-chlorothiophene-2-yl, 2,5-dichlorothiophene-3-yl, benzothiophene-2-yl, 3-chlorobenzothiophene-2-yl, isoxazol-5-yl, 5-methylisoxazol-3-yl, 3,5-dimethylisoxazol-4-yl, 1,3-dimethylpyrazol-5-yl, 1-ethyl-3-methylpyrazol-5-yl, 1-tertbutyl-3-methylpyrazol-5-yl, 3-tert-butyl-1-methylpyrazol-5-yl, 4-bromo-1-ethyl-3-methylpyrazol-5-yl, indole-3-ylcarboxyl, pyridinyl, chloropyridinyl, dichloropyridinyl, 5-(bromo)pyridin-3-yl, piperazin-2-yl, quinoxal-2-yl;
fluoromethyl, difluoromethyl, trifluoromethyl, 1,1,2,2-tetrafluoroethyl, pentafluoroethyl, heptafluoropropyl, 1,1,2,2,3,3,4,4-octafluorobutyl, nonafluorobutyl, chloromethyl, chloroethyl, 1,1-dimethyl-2-chloroethyl, 1,2-dichloroethyl, 1-chloropropyl, 3-chloropropyl,4-chlorobutyl, hydroxymethyl, methoxymethyl, phenoxymethyl, (4-chlorophenoxy)methyl, benzyloxymethyl, acetoxymethyl, 1,2-dihydroxyethyl, 1-phenoxyethyl, 1-acetoxyethyl, 2-(2-carboxyethoxy)ethyl, 1-phenoxyethyl, 1-acetoxyethyl, methoxycarbonyl, ethoxycarbonyl, (methoxycarbonyl)methyl, 2-carboxyethyl, 2-(methoxycarbonyl)ethyl, 2-carboxycyclopropyl, 2-carboxycyclohexane;
methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, pentoxy, neopentoxy, hexyloxy, cyclopentyloxy, cyclohexyloxy, vinyloxy, allyloxy, propargyloxy, chloromethoxy, 1-chloroethoxy, 2-methoxyethoxy, 4-chlorobutoxy, phenoxy, 4-methylphenoxy, 4-fluorophenoxy, 4-bromophenoxy, 4-chlorophenoxy, 4-methoxyphenoxy, naphth-2-yloxy, benzyloxy; amino, methylamino, ethylamino, propylamino, isopropylamino, butylamino, cyclohexylamino, allylamino, 2-chloroethylamino, 3-chloropropylamino, carboxymethylamino, phenylamino, fluorophenylamino, (trifluoromethyl)phenylamino, chlorophenylamino, bromophenylamino, 4-acetylphenylamino, methoxyphenylamino, (trifluoromethoxy)phenylamino, naphth-1-ylamino, benzylamino, phenethylamino, pyrid-3-ylamino, dimethylamino, 1-pyrolidinyl, 4-morpholinyl. 6. Compounds according to any one of the preceding claims, characterized in that R1 and R2 form a cycle, said cycle being selected from 2-pyrrolidinon-1-yl, methyl-2-pyrrolidinon-1-yl groups, 5-Carboxy-2-pyrrolidinon-1-yl, 5-methoxycarbonyl-2-pyrrolidinon-1-yl, pyrazolinone-1-yl, succinimide-1-yl, 3,5-diketopyrazolidin-1-yl, oxindolin-1-yl, maleimide-1yl, isoindole-1,3-dione-2-yl, 2-piperidinone-1-yl, and glutarimide-1-yl. 7. Compounds according to claim 4, characterized in that R2 represented a radical chosen from the group (G2) consisting of a methyl radical, ethyl, propyl, allyl, phenyl, tetrahydrofuran-2-yl, furan-2-yl, thiophene-2-yl, pyridinyl, piperazin-2-yl, fluoromethyl, chloromethyl, 2-chloroethyl, methoxymethyl, acetoxymethyl, 1,2-dihydroxyethyl, methoxycarbonyl, 2-carboxyethyl, methoxy, ethoxy, propoxy, allyloxy, 2-chloroethoxy, 2-methoxyethoxy, amino, ethylamino, allylamino, 2-chloroethylamino, pyridylamino, dimethylamino, 1-pyrolidinyl, and 4-morpholinyl; or one group -D1, -E-D1, -OE-D1, -NH-E-D1, in which -E- represents a arm -(CH2)q-, q being an integer equal to 1 or 2, and D, represents a group D' chosen from 3-methylimidazolidinium-1-yl groups, 3-(2-hydroxyethyl)-imidazolidinium-1-yl, 1,2,4-triazolinium-1-yl, 1,2,4-triazolinium-4-yl, N-alkyl(C1-C4)pyridinium-2-yl, N-alkyl(C1-C4)pyridinium-3-yl, N-alkyl(C1-C4)pyridinium-4-yl, N-(2-hydroxyethyl)pyridinium-2-yl, N-(2-hydroxyethyl)pyridinium-3-yl, N-(2-hydroxyethyl)pyridinium-4-yl, pyridinium-1-yl, trialkyl(C1-C4)ammonium-N-yl, 1-methylpiperidinium-1-yl and 1,4-dimethylpiperazinium-1-yl. 8. Compounds according to claim 7, characterized in that R2 represented a methyl, methoxymethyl, 2-carboxyethyl, methoxy, amino, ethylamino, or 1-pyrolidinyl; or a group -D1, -E-D1, -OE-D1, -NH-E-D1, in which -E- represents a -(CH2)q- arm, q=1 to 2, and D1 a group D' as defined in claim 7. 9. Compounds according to any one of the preceding claims, characterized in that R3 and R4, which are identical or different, denote a hydrogen or halogen atom; a hydroxyl or amino group; a Z group; an A1 group as defined in claim 2; a group A1, A2, A3, A4 or A5 as defined in claim 2 and separated of the phenolic nucleus of formula (II) by an oxygen atom or by a group -NH-, -Nalkyl(C1-C3)-, -NH(CO)-, -Nalkyl(C1-C3)CO)-, -NH[C=NH]-, -NH(CO)NH-, -NH(CO)Nalkyl(C1-C3), -NH(CO)O-, -NHSO2-, -NHSO2NH-, or -NHSO2Nalkyl(C1-C3)-. 10. Compounds according to claim 9, characterized in that R3 represents a hydrogen or chlorine atom; a Z group; a radical methyl, hydroxymethyl, methoxymethyl, 1-hydroxyethyl, aminomethyl, methylaminomethyl, hydroxy, methoxy, amino, methylamino, or 2-hydroxyethylamino; an -NH(CO)R12 group in which R12 represents one of the radicals listed in the group (G1) as defined in claim 5 ;
a group -NHSO2R13, in which R13 represents one of the radicals listed in the group (G3) consisting of the methyl, trifluoromethyl, ethyl, 2-chloroethyl, propyl, 3-chloropropyl, isopropyl, butyl, thiophene-2-yl, hydroxy, ethoxy and dimethylamino. 11. Compounds according to claim 10, characterized in that R3 represents a hydrogen atom; a methyl or hydroxymethyl radical, aminomethyl, hydroxy, methoxy, amino, methylamino; a group methanesulfonylamino; ethanesulfonylamino; dimethylamino-sulfonylamino;
a -NH(CO)R14 group in which R14 represents one of the radicals listed in the group (G2) as defined in claim 7; or a group -OE-D2, -NH-E-D2, -NH(CO)-D2, -NH(CO)-E-D2, -NH(CO)OE-D2, -NH(CO)NH-E-D2, or -NH(SO2)-E-D2, in which -E- has the same meaning than that indicated in claim 7 and D2 represents a group D' as defined in claim 7. 12. Compounds according to claim 9, characterized in that R4 represents a hydrogen or chlorine atom; a Z group; a radical methyl, ethyl, hydroxymethyl, methoxymethyl, aminomethyl, methylaminomethyl, hydroxy, methoxy, acetoxy, amino, methylamino, N-piperidino, or N-morpholino; a -NH(CO)R15 group in which R15 represents one of the radicals listed in the group (G1) defined in claim 5; or a -NHSO2R16 group in which R16 represents one radicals listed in the group (G3) defined in claim 10. 13. Compounds according to claim 12, characterized in that R4 represents a hydrogen or chlorine atom; a methyl radical, hydroxymethyl, aminomethyl, hydroxy, methoxy, amino, or methylamino; a methanesulfonylamino group; ethanesulfonylamino;
dimethylaminosulfonylamino; a -NH(CO)R17 group in which R17 represents one of the radicals listed in the group (G2) defined in claim 7; or a group -OE-D3, -NH-E-D3, -NH(CO)-D3, -NH(CO)-E-D3, -NH(CO)OE-D3, -NH(CO)NH-E-D3, or -NH(SO2)-E-D3, wherein -E- has the same meaning as set out in claim 7, and D3 represented a group D' as defined in claim 7. 14. Compounds according to any one of the preceding claims, characterized in that R5 is chosen from a hydrogen atom or halogen; a Z group; an A1 group as defined in claim 2; an A1, A2, A3, A4 or A5 group as defined in claim 2 and separated from the phenolic core of the compounds of formula (II) by an oxygen or sulfur atom, or by an -NH- group, -Nalkyl(C1-C3-NH(CO)-, -Nalkyl(C1-C3)(CO)-, -NH[C=NH]-, -NH(CO)NH-, -NH(CO)Nalkyl(C1-C3)-, or -NH(CO)O-. 15. Compounds according to claim 14, characterized in that R5 represents a hydrogen, chlorine, fluorine or bromine atom; a Z group; a methyl, trifluoromethyl, allyl, methoxy, or methylamino; or an -NH(CO)R18 group in which R18 represents one radicals listed in the group (G1) defined in claim 5. 16. Compounds according to claim 15, characterized in that R5 represents a hydrogen, chlorine or fluorine atom; a methyl radical, methoxy; or methylamino; a -NH(CO)R19 group in which R19 represents one of the radicals listed in the group (G2) defined in claim 7; or a group -OED,, -NH-E-D4, -NH(CO)-D4, -NH(CO)-E-D4, -NH(CO)OE-D4, -NH(CO)NH-E-D4, wherein -E- has the same meaning as indicated in claim 7, and D4 represents a group D' as defined in claim 7. 17. Compounds according to any one of the preceding claims, characterized in that Y is chosen from a hydrogen atom, chlorine, fluorine, or bromine; a methoxy, ethoxy, propoxy, benzyloxy group, phenoxy, -OCH2CH2OCH3; -OCH2CH2OCH3; -OCH2CH2N(CH3)2; -OCH2(CO)OH, -OCH2(CO)OCH3, -OCH2(CO)OC2H5, -SCH2CH2CO2H, or -NHSO2CH3; being understood that Y cannot represent a -NHSO2CH3 group when R3 represents a hydroxyl radical. 18. Compounds according to any one of the preceding claims, characterized in that D is chosen from imidazolinium groups, thiazolinium, oxazolinium, pyrrolinium, 1,2,3-triazolinium, 1,2,4-triazolinium, isoxazolinium, ixothiazolinium, imidazolidinium, thiazolidinium, pyrazolinium, pyrazolidinium, oxazolidinium, pyrazoltriazolinium, pyrazoloimidazolinium, pyrrolotriazolinium, pyrazolopyrimidinium, pyrazolopyridinium, pyridinium, pyrimidinium, pyrazinium, triazinium, benzoimidazolinium, benzoxazolinium, benzothiazolinium, indolinium, indolidinium, isoindolinium, indazolinium, benzotriazolinium, quinolinium, tetrahydroquinolinium, benzoimidazolidinium, benzopyrimidinium, tetra-alkyl(C1-C4)ammonium, polyhydroxyltetra-alkyl(C1-C4)ammonium, dialkylpiperidinium, dialkylpyrrolidinium, dialkylmorpholinium, dialkylthiomorpholinium, dialkylpiperazinium, azepinium, and 1,4-diazabicyclo[2,2,2]octanium. 19. Compounds according to claim 18, characterized in that D
represents a 3-methylimidazolidinium-1-yl, 3-(2-hydroxyethyl)- group imidazolidinium-1-yl, 1,2,4-triazolinium-1-yl, 1,2,4-triazolinium-4-yl, N-alkyl(C1-C4)pyridinium-2-yl, N-alkyl(C1-C4)pyridinum-3-yl, N-alkyl(C1-C4)pyridinum-4-yl, N-(2-hydroxyethyl)pyridinum-2-yl, N-(2-hydroxyethyl)pyridinum-3-yl, N-(2-hydroxyethyl)pyridinum-4-yl, pyridinum-1-yl, trialkyl(C1-C4)ammonium-N-yl, 1-methylpiperidinium-1-yl, 1,4-dimethylpiperazinium-1-yl. 20. Compounds according to any one of the preceding claims, characterized in that A represents an imidazolidinium group, N-alkyl(C1-C4)pyridinium, N-(2-hydroxyethyl)pyridinium, pyridinium, dialkyl(C1-C4)ammonium, 1,4-dimethylpiperazinium-1-yl. 21. Compounds according to any one of the preceding claims, characterized by the fact that B, B1 and B2, independently of each other, represent a -(CH2)-, -(CH2)-(CH2)-, or -(CH2)-(CH2)-(CH2)- arm. 22. Compounds according to any one of the preceding claims, characterized by the fact that they are chosen from - 1,3-bis-[(2-hydroxy-phenylcarbamoyl)-methyl]-3H-imidazol-1- chloride ium;
- 1,3-bis-[(2-hydroxy-4-methyl-phenylcarbamoyl)-methylJ-3H- chloride imidazol-1-ium;
- 1,3-bis-[(2-hydroxy-4-amino-phenylcarbamoyl)-methyl]-3H- chloride imidazol-1-ium;
- 1,3-bis-[(2-hydroxy-4-acetylamino-phenylcarbamoyl)-methyl]- chloride 3H-imidazol-1-ium;
- 1,3-bis-[(2-hydroxy-4-methoxycarbonylamino-phenylcarbamoyl) chloride"
methyl]-3H-imidazol-1-ium;
- 1,3-bis-[(3-hydroxy-4-acetylamino-phenylcarbamoyl)-methyl] chloride-3H-imidazol-1-ium;
- 1,3-bis-[(3-hydroxy-4-methoxycarbonylamino-phenylcarbamoyl) chloride-methyl]-3H-imidazol-1-ium;
- 1,3-bis-[(2-hydroxy-5-chloro-phenylcarbamoyl)-methyl]-3H- chloride imidazol-1-ium;
- 1,3-bis-[(2-hydroxy-4-methyl-5-chloro-phenylcarbamoyl) chloride-methyl]-3H-imidazol-1-ium;
- 1,3-bis-[(2-hydroxy-4-amino-5-chloro-phenylcarbamoyl)-methyl]- chloride 3H-imidazol-1-ium;
- 1,3-bis-[(2-hydroxy-4-acetylamino-5-chloro-phenylcarbamoyl) chloride-methyl]-3H-imidazol-1-ium;
- 1,3-bis-[(2-hydroxy-4-methoxycarbonylamino-5-chloro-) chloride phenylcarbamoyl)-methyl]-3H-imidazol-1-ium;
- 1,3-bis-[(3-hydroxy-4-acetylamino-5-chloro-phenylcarbamoyl) chloride-methyl]-3H-imidazol-1-ium;
- 1,3-bis-[(3-hydroxy-4-methoxycarbonylamino-6-chloro-) chloride phenylcarbamoyl)-methyl]-3H-imidazol-1-ium;
- 1,3-bis-[(2-hydroxy-5-methoxy-phenylcarbamoyl)-methyl]-3H- chloride imidazol-1-ium;
- 1,3-bis-[(2-hydroxy-4-methyl-5-methoxy-phenylcarbamoyl) chloride-methyl)-3H-imidazol-1-ium;
- 1,3-bis-[(2-hydroxy-4-amino-5-methoxy-phenylcarbamoyl) chloride-methyl]-3H-imidazol-1-ium;
- 1,3-bis-[(2-hydroxy-4-acetylamino-5-methoxy-) chloride phenylcarbamoyl)-methyl]-3H-imidazol-1-ium;
- 1,3-bis-[(2-hydroxy-4-methoxycarbonylamino-5-methoxy-) chloride phenylcarbamoyl)-methyl]-3H-imidazol-1-ium;
- 1,3-bis-[(3-hydroxy-4-acetylamino-6-methoxy-) chloride phenylcarbamoyl)-methyl]-3H-imidazol-1-ium;
- 1,3-bis-[(3-hydroxy-4-methoxycarbonylamino-6-methoxy) chloride phenylcarbamoyl)-methyl]-3H-imidazol-1-ium;

- 1,3-bis-[(2-hydroxy-6-amino-phenylcarbamoyl)-methyl]-3H- chloride imidazol-1-ium;
- 1,3-bis-[(2-hydroxy-6-acetylamino-phenylcarbamoyl)-methylj-chloride 3H-imidazol-1-ium;
- 1,3-bis-[(2-hydroxy-4,6-diamino-phenylcarbamoyl)-methyl]-3H- chloride imidazol-1-ium;
- 1,3-bis-[(2-hydroxy-4-acetylamino-6-amino-phenylcarbamoyl) chloride-methyl]-3H-imidazol-1-ium;
- 1,3-bis-[(2-hydroxy-3,5-dichloro-4-methyl-phenylcarbamoyl) chloride-methyl]-3H-imidazol-1-ium;
- 1,3-bis-[(2-hydroxy-3,5-dichloro-4-amino-phenylcarbamoyl~ chloride) methyl]-3H-imidazol-1-ium;
- 1,3-bis-[(2-hydroxy-3,5-dichloro-4-acetylamino-phenylcarbamoyl)-methyl]-3H-imidazol-1-ium;
- 1,3-bis-[(2-hydroxy-3,5-dichloro-4-methoxycarbonylamino-phenylcarbamoyl)-methyl]-3H-imidazol-1-ium;
- 1,3-bis-[(2-hydroxy-3-acetylamino-phenylcarbamoyl)-methyl]- chloride 3H-imidazol-1-ium;
- 3-[(2-hydroxy-4-amino-phenylcarbamoyl)-methyl]-1-[(2-hydroxy-4-Methyl-phenylcarbamoyl)-methyl)-3H-imidazol-1-ium;
- 3-[(2-hydroxy-3,5-dichloro-4-methyl-phenylcarbamoyl)-methyl]- chloride 1-[(2-hydroxy-4-methyl-phenylcarbamoyl)-methyl]-3H-imidazol-1-ium;
- 1,4-bis-[(2-hydroxy-phenylcarbamoyl)-methyl]-1-methyl-chloride piperazin-1-ium;
- 1,4-bis-[(2-hydroxy-4-methyl-phenylcarbamoyl)-methyl]-1-chloride methyl-piperazin-1-ium;
- 1,4-bis-[(2-hydroxy-4-amino-phenylcarbamoyl)-methyl]-1-chloride methyl-piperazin-1-ium;
- 1,4-bis-[(2-hydroxy-4-acetylamino-phenylcarbamoyl)-methyl]-1-chloride methyl-piperazin-1-ium;
- 1,4-bis-[(2-hydroxy-4-methoxycarbonylamino-phenylcarbamoyl~ chloride) methyl]-1-methyl-piperazin-1-ium;
- 1,4-bis-[(3-hydroxy-4-acetylamino-phenylcarbamoyl)-methyl]-1-chloride methyl-piperazin-1-ium;
- 1,4-bis-[(3-hydroxy-4-methoxycarbonylamino-phenylcarbamoyl) chloride-methyl]-1-methyl-piperazin-1-ium;
- 1,4-bis-[(2-hydroxy-5-chloro-phenylcarbamoyl)-methyl]-1-chloride methyl-piperazin-1-ium;
- 1,4-bis-[(2-hydroxy-4-methyl-5-chloro-phenylcarbamoyl) chloride-methyl]-1-methyl-piperazin-1-ium;
- 1,4-bis-[(2-hydroxy-4-amino-5-chloro-phenylcarbamoyl)-methyl]- chloride 1-methyl-piperazin-1-ium;
- 1,4-bis-[(2-hydroxy-4-acetylamino-5-chloro-phenylcarbamoyl) chloride-methyl]-1-methyl-piperazin-1-ium;
- 1,4-bis-[(2-hydroxy-4-methoxycarbonylamino-5-chloro-) chloride phenylcarbamoyl)-methyl]-1-methyl-piperazin-1-ium;
- 1,4-bis-[(3-hydroxy-4.-acetylamino-6-chloro-phenylcarbamoyl) chloride-methyl]-1-methyl-piperazin-1-ium;
- 1,4-bis-[(3-hydroxy-4-methoxycarbonylamino-6-chloro-) chloride phenylcarbamoyl)-methyl]-1-methyl-piperazin-1-ium;
- 1,4-bis-[(2-hydroxy-5-methoxy-phenylcarbamoyl)-methyl]-1-chloride methyl-piperazin-1-ium;
- 1,4-bis-[(2-hydroxy-4-methyl-5-methoxy-phenylcarbamoyl) chloride-methyl]-1-methyl-piperazin-1-ium;
- 1,4-bis-[(2-hydroxy-4-amino-5-methoxy phenylcarbamoyl) chloride-methyl]-1-methyl-piperazin-1-ium;
- 1,4-bis-[(2-hydroxy-4-acetylamino-5-methoxy-) chloride phenylcarbamoyl)-methyl]-1-methyl-piperazin-1-ium;
- 1,4-bis-[(2-hydroxy-4-methoxycarbonylamino-5-methoxy-) chloride phenylcarbamoyl)-methyl]-1-methyl-piperazin-1-ium;
- 1,4-bis-[(3-hydroxy-4-acetylamino-6-methoxy-) chloride phenylcarbamoyl)-methyl]-1-methyl-piperazin-1-ium;

- 1,4-bis-[(3-hydroxy-4-methoxycarbonylamino-6-methoxy) chloride phenylcarbamoyl)-methyl]-1-methyl-piperazin-1-ium;
- 1,4-bis-[(2-hydroxy-6-amino-phenylcarbamoyl)-methyl]-1-chloride methyl-piperazin-1-ium;
- 1,4-bis-[(2-hydroxy-6-acetylamino-phenylcarbamoyl)-methyl]-1-chloride methyl-piperazin-1-ium;
- 1,4-bis-[(2-hydroxy-4,6-diamino-phenylcarbamoyl)-methyl]-1-chloride methyl-piperazin-1-ium;
- 1,4-bis-[(2-hydroxy-4-acetylamino-6-amino-phenylcarbamoyl) chloride-methyl]-1-methyl-piperazin-1-ium;
- 1,4-bis-[(2-hydroxy-3,5-dichloro-4-methyl-phenylcarbamoyl) chloride-methyl]-1-methyl-piperazin-1-ium;
- 1,4-bis-[(2-hydroxy-3,5-dichloro-4-amino-phenylcarbamoyl) chloride-methyl]-1-methyl-piperazin-1-ium;
- 1,4-bis-[(2-hydroxy-3,5-dichloro-4-acetylamino-) chloride phenylcarbamoyl)-methyl]-1-methyl-piperazin-1-ium;
- 1,4-bis-[(2-hydroxy-3,5-dichloro-4-methoxycarbonylamino-phenylcarbamoyl)-methyl]-1-methyl-piperazin-1-ium;
- 1,4-bis-[(2-hydroxy-3-acetylamino-phenylcarbamoyl)-methyl]-1-chloride methyl-piperazin-1-ium;
and their addition salts with an acid. 23. Compounds according to any one of the preceding claims, characterized in that the addition salts with an acid are chosen among hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates and acetates. 24. Use of compounds of formula (I) as defined in one any of claims 1 to 23, as a coupler for oxidation dyeing of the keratin fibers. 25. Composition for oxidation dyeing of keratin fibres, characterized in that it contains, in a medium suitable for the dyeing:
- at least one oxidation base, and - at least one coupler chosen from the compounds of formula (I) such as defined in any one of claims 1 to 23. 26. Composition according to claim 25, characterized in that the or them compounds of formula (I) and/or the addition salt(s) thereof with an acid represent from 0.0005 to 12% by weight of the total weight of the composition tinctorial. 27. Composition according to claim 25 or 26, characterized in that the or the oxidation bases are chosen from para-phenylenediamines, bis-phenylalkylenediamines, para-aminophenols, ortho-aminophenols and heterocyclic bases, and their addition salts with an acid. 28. Composition according to any one of claims 25 to 27, characterized in that the oxidation base or bases represent 0.0005 to 12% by weight of the total weight of the dye composition. 29. Composition according to any one of claims 25 to 28, characterized in that it additionally contains the compound(s) of formula (I) above, one or more additional couplers selected from the meta-phenylenediamines, meta-aminophenols, meta-diphenols and heterocyclic couplers, and their addition salts with an acid, and/or one or several direct dyes. 30. Composition according to claim 29, characterized in that the or them additional couplers represent from 0.0001 to 10% by weight of the total weight of the dye composition. 31. Composition according to any one of claims 25 to 30, characterized in that the addition salts with an acid are chosen among hydrochlorides, hydrobromides, sulphates, citrates, succinct, tartrates, lactates and acetates. 32. Process for the oxidation dyeing of keratin fibres, characterized by the fact that at least one dye composition is applied to these fibers such as defined in any one of claims 25 to 31, and which is disclosed the color at acidic, neutral or alkaline pH using an oxidizing agent which is added just at the time of use to the dye composition or which is present in an oxidizing composition applied simultaneously or sequentially separate way. 33. Process according to claim 32, characterized in that the agent oxidant is chosen from hydrogen peroxide, urea peroxide, bromates of alkali metals, persalts, and enzymes. 34. Multi-compartment device, or multi-dye "kit"
compartments, of which a first compartment contains a composition dye as defined in any one of claims 25 to 31 and a second compartment contains an oxidizing composition.